Stereoselective syntheses and reactions of chiral oxygenated α,β-unsaturated-γ- and δ-lactones

Tetrahedron Asymmetry

Volumn 7, Issue 11, 1996, Pages 3209-3246

  Sánchez Sancho, Francisco ^a   Valverde, Serafín ^a   Herradón, Bernardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANAMARINE; ASPERLIN; GAMMA LACTONE DERIVATIVE; OLGUINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030575792     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00424-7     Document Type: Article

References (227)

1. (1) Davies-Coleman, M. T.; Rivett, D. E. A. Prog. Chem. Nat. Prod. 1989, 55, 1-35. Jefford, C. W.; Jaggi, D.; Sledeski, A. W.; Boukouvalas, J. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: Amsterdam; 1989; vol 3, pp 157-171.
2. (1) Davies-Coleman, M. T.; Rivett, D. E. A. Prog. Chem. Nat. Prod. 1989, 55, 1-35. Jefford, C. W.; Jaggi, D.; Sledeski, A. W.; Boukouvalas, J. In Studies in Natural Products Chemistry; Rahman, A., Ed.; Elsevier: Amsterdam; 1989; vol 3, pp 157-171.
3. (2) For some recent references on biologically active lactones, see: Tsuda, M.; Shigemori, H.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 3503-3507. Lehmann, J.; Pieper, B. Tetrahedron: Asymmetry 1992, 3, 1537-1538. Dai, W.; Katzenellenbogen, J. A. J. Org. Chem. 1993, 58, 1900-1908. Gravier-Pelletier, C.; Sanière, M.; Charvet, I.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 115-118. Lee, J.; Marquez, V.; Lewin, N. E.; Blumberg, P. M. Synlett 1994, 206-208.
4. (2) For some recent references on biologically active lactones, see: Tsuda, M.; Shigemori, H.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 3503-3507. Lehmann, J.; Pieper, B. Tetrahedron: Asymmetry 1992, 3, 1537-1538. Dai, W.; Katzenellenbogen, J. A. J. Org. Chem. 1993, 58, 1900-1908. Gravier-Pelletier, C.; Sanière, M.; Charvet, I.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 115-118. Lee, J.; Marquez, V.; Lewin, N. E.; Blumberg, P. M. Synlett 1994, 206-208.
5. (2) For some recent references on biologically active lactones, see: Tsuda, M.; Shigemori, H.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 3503-3507. Lehmann, J.; Pieper, B. Tetrahedron: Asymmetry 1992, 3, 1537-1538. Dai, W.; Katzenellenbogen, J. A. J. Org. Chem. 1993, 58, 1900-1908. Gravier-Pelletier, C.; Sanière, M.; Charvet, I.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 115-118. Lee, J.; Marquez, V.; Lewin, N. E.; Blumberg, P. M. Synlett 1994, 206-208.
6. (2) For some recent references on biologically active lactones, see: Tsuda, M.; Shigemori, H.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 3503-3507. Lehmann, J.; Pieper, B. Tetrahedron: Asymmetry 1992, 3, 1537-1538. Dai, W.; Katzenellenbogen, J. A. J. Org. Chem. 1993, 58, 1900-1908. Gravier-Pelletier, C.; Sanière, M.; Charvet, I.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 115-118. Lee, J.; Marquez, V.; Lewin, N. E.; Blumberg, P. M. Synlett 1994, 206-208.
7. (2) For some recent references on biologically active lactones, see: Tsuda, M.; Shigemori, H.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 3503-3507. Lehmann, J.; Pieper, B. Tetrahedron: Asymmetry 1992, 3, 1537-1538. Dai, W.; Katzenellenbogen, J. A. J. Org. Chem. 1993, 58, 1900-1908. Gravier-Pelletier, C.; Sanière, M.; Charvet, I.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron Lett. 1994, 35, 115-118. Lee, J.; Marquez, V.; Lewin, N. E.; Blumberg, P. M. Synlett 1994, 206-208.
8. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
9. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
10. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
11. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
12. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
13. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
14. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
15. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
16. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
17. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
18. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
19. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
20. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
21. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
22. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
23. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
24. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
25. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
26. (3) For some recent synthesis of biologically active compounds using chiral lactones as intermediates, see: Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron 1992, 48, 10363-10376 (ß-lactams). Herdeis, C.; Lütsch, K. Tetrahedron: Asymmetry 1993, 4, 121-131 (amino hydroxy acids). Casiraghi. G.; Rassu, G.; Spanu, P.; Pinna, P.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400 (polyhydroxylated alkaloids). Tanaka, M.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Synlett 1994, 604-605 (lignans). Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412 (C-glycosides). Ferreira, J. T. B.; Marques, J. A.; Marino, J. P. Tetrahedron: Asymmetry 1994, 5, 641-648 (pheromones). Hanessian, S.; Girard, C. Synlett 1994, 865-867 (higher carbon sugars). Po, S.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1869-1872 (amino sugars). Shiozaki, M.; Kobayashi, Y.; Arai, M.; Haruyama, H. Tetrahedron Lett. 1994, 35, 887-890 (glycosidase inhibitors). Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem, 1995, 60, 7927-7933 (peptidomimetics). Paquette, L. A.; Wang, T.-Z.; Pinard, E. J. Am. Chem. Soc. 1995, 117, 1455-1456 (diterpenes). Nemoto, H.; Tanabe, T.; Fukumoto, K. J. Org. Chem. 1995, 60, 6785-6790 (alkaloids). Nacro, K.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1995, 36, 7867-7870 (nucleosides). Martín, T.; Rodríguez, C. M.; Martín, V. S. Tetrahedron: Asymmetry 1995, 6, 1151-1164 (monoterpenes). Figadère, B. Acc. Chem. Res. 1995, 28, 359-365 (acetogenins). Estévez, J. C.; Smith, M. D.; Wornald, M. R.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 391-394 (glycopeptides). For iterative transformations using chiral lactones as intermediates, see: Ziegler, F. E.; Wester, R. T. Tetraheron Lett. 1986, 27, 1225-1228. Stork, G.; Rychnovsky, S. D. J. Am. Chem. Soc. 1987, 109, 1564-1565. Hanessian, S. Aldrichimica Acta 1989, 22, 3-15, and references cited therein.
27. (4) Itoh, K.; Takeda, M.; Namekawa, M.; Nayuki, S.; Murayama, Y.; Yamazaki, T.; Kitazume, T. Chem. Lett. 1994, 839-842; and references cited therein.
28. (5) For some books and reviews on this topic, see: Stereochemistry and Biological Activity of Drugs; Ariëns, E. J., Soudijn, W., Timmermans, P. B. M. W. M., Eds.; Blackwell Scientific Publications: Oxford; 1983. Ramos-Tombo, G. M.; Bellus, D. Angew. Chem. Int. Ed. Engl. 1991, 30, 1193-1215. Crossley, R. Tetrahedron 1992, 48, 8155-8178.
29. (5) For some books and reviews on this topic, see: Stereochemistry and Biological Activity of Drugs; Ariëns, E. J., Soudijn, W., Timmermans, P. B. M. W. M., Eds.; Blackwell Scientific Publications: Oxford; 1983. Ramos-Tombo, G. M.; Bellus, D. Angew. Chem. Int. Ed. Engl. 1991, 30, 1193-1215. Crossley, R. Tetrahedron 1992, 48, 8155-8178.
30. (5) For some books and reviews on this topic, see: Stereochemistry and Biological Activity of Drugs; Ariëns, E. J., Soudijn, W., Timmermans, P. B. M. W. M., Eds.; Blackwell Scientific Publications: Oxford; 1983. Ramos-Tombo, G. M.; Bellus, D. Angew. Chem. Int. Ed. Engl. 1991, 30, 1193-1215. Crossley, R. Tetrahedron 1992, 48, 8155-8178.
31. (6) For a definition and discussion, see: Seebach, D.; Hungerbuhler, E. In Modern Synthetic Methods; Scheffold, R. Ed.; Salle and Sauerländer: Berlin; 1980; Vol. 2, pp 91-171.
32. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
33. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
34. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
35. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
36. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
37. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
38. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
39. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
40. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
41. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
42. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
43. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
44. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
45. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
46. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
47. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
48. (7) Koch, S. C.; Chamberlin, A. R. J. Org. Chem. 1993, 58, 2725-2737, and references cited therein. For more recent papers on the EPC-synthesis of lactones, see: Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1994, 59, 7201-7208. Rodriguez, C. M.; Martín, T.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 1994, 59, 4461-4472. Tiedermann, R.; Narjes, F.; Schaumann, E. Synlett 1994, 594-596. Trincone, A.; Pagnotta, E.; Sodano, G. Tetrahedron Lett. 1994, 35, 1415-1416. Fellous, R.; Lizzani-Cuvelier, L.; Loiseau, M. A.; Sassy, E. Tetrahedron: Asymmetry 1994, 5, 343-346. Luna, H.; Prasad, K.; Repic, O. Tetrahedron: Asymmetry 1994, 5, 303-306. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365-369. Hoye, T. R.; Hanson, P. R.; Hasenwinkel, L. E.; Ramirez, E. A.; Zhuang, Z. Tetrahedron Lett. 1994, 35, 8525-8528. Moon, H.; Schore, N. E.; Kurth, M. J. Tetrahedron Lett. 1994, 35, 8915-8918. Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494. Doyle, M. P.; Dyatkin, A. B.; Roos, G. H. P.; Cañas, F.; Pierson, D. A.; van Basten, A.; Müller, P.; Polleux, P. J. Am. Chem. Soc. 1994, 116, 4507-4508. Kanai, M.; Tomioka, K. Tetrahedron Lett. 1995, 36, 4275-4278. Taylor, S. K.; Atkinson, R. F.; Almli, E. P.; Carr, M. D.; Van Huis, T. J.; Whittaker, M. R. Tetrahedron: Asymmetry 1995, 6, 157-164. Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 5063-5064. Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 9-12. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428-2440. Ottolina, G.; Carrea, G.; Colonna, S.; Rückemann, A. Tetrahedron: Asymmetry 1996, 7, 1123-1136.
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86. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
87. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
88. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
89. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
90. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
91. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
92. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
93. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
94. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
95. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
96. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
97. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
98. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
99. 18 the Wittig reaction in alcoholic solvents has been more frequently used; for some references, see; Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391-402. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640. Krief, A.; Dumont, W.; Pasau, P.; Lecomte, P. Tetrahedron 1989, 45, 3039-3052. Kang, S.-K.; Lee, D.-H.; Kim, S.-G. Org. Prep. Proc. Int. 1990, 22, 651-654. Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans I 1992, 1907-1910. Prakash, K. R. C.; Rao, S. P. Synlett. 1993, 123-124. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691-692. Palazón, J. M.; Soler, M. A.; Ramírez, M. A.; Martín, V. S. Tetrahedron Lett. 1993, 34, 5467-5470. Hueso-Rodríguez, J. A.; Berrocal, J.; Gutiérrez, B.; Farré A. J.; Frigola, J. Bioorg. Med. Chem. Lett. 1993, 3, 269-272. Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 35, 9047-9050. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Kan, T.; Oikawa, M.; Hosokawa, S.; Yanagiya, M.; Matsuda, F.; Shirahama, H. Synlett 1994, 805-808. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121-3130.
100. (20) For a preliminary disclosure on the synthesis of (+)-5, see: Valverde, S.; Herradón, B.; Martín-Lomas, M. Tetrahedron Lett. 1985, 26, 3731-3734.
101. (21) For a preliminary communication on the synthesis of (-)-6, see: Herradón, B. Tetrahedron: Asymmetry 1991, 2, 191-194.
102. (22) Hizuka, M.; Hayashi, N.; Kamashita, T.; Suemune, H.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 1550-1553.
103. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
104. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
105. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
106. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
107. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
108. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
109. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
110. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
111. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
112. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
113. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
114. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
115. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
116. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
117. (23) For other syntheses of (+)-eldanolide, see: Uematsu, T.; Umemura, T.; Mori, K. Agric. Biol. Chem. 1983, 47, 597-601. Vigneron, J. P.; Méric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529. Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861-864. Davies, H. G.; Roberts, S. M.; Wakefield, B. J.; Winders, J. A. J. Chem. Soc., Chem. Commun. 1985, 1166-1168. Matteson, D. S.; Sadhu, K. M.; Peterson, M. L. J. Am. Chem. Soc. 1986, 108, 810-819. Ortuño, R. M.; Mercé, R.; Font, J. Tetrahedron Lett. 1986, 27, 2519-2522. Larchevêque, M.; Tamagnan, G.; Petit, Y. J. Chem. Soc., Chem. Commun. 1989, 31-33. Bloch, R. Seck, M. Tetrahedron 1989, 45, 3731-3740. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667-5670. Suzuki, Y.; Mori, W.; Ishizone, H.; Naito, K.; Honda, T. Tetrahedron Lett. 1992, 33, 4931-4932. Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Okano, K.; Matsushita, H. Heterocycles 1993, 6, 1017-1026. Mobbili, G.; Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1993, 230-231. Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253-2260. Honda, T.; Yamane, S.; Naito, K.; Suzuki, Y. Heterocycles 1994, 37, 515-521. Angert, H.; Czerwonka, R.; Reißig, H.-U. Liebigs Ann. 1996, 259-263.
118. (24) Hizuka, M.; Fang, C.; Suemune, H.; Sakai, K. Chem. Pharm. Bull. 1989, 37, 1185-1187.
119. (25) Tanaka, M.; Murakami, T.; Suemune, H.; Sakai, K. Heterocycles 1992, 33, 697-700.
120. (26) For other synthesis of the (+)-Geissman-Waiss lactone, as well as its applications in pyrrolizidine alkaloid syntheses, see: Shishido, K.; Sukegawa, Y.; Fukumoto, K.; Kametani, T. Heterocycles 1985, 23, 1629-1633. Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc., Chem. Comm. 1988, 509-510. Nagao, Y.; Dai, W.-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211-5217. Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393-412. Paolucci, C.; Venturelli, F.; Fava, A. Tetrahedron Lett. 1995, 36, 8127-8128. Liddell, J. R. Nat. Prod. Rep. 1996, 13, 187-193, and references cited therein.
121. (26) For other synthesis of the (+)-Geissman-Waiss lactone, as well as its applications in pyrrolizidine alkaloid syntheses, see: Shishido, K.; Sukegawa, Y.; Fukumoto, K.; Kametani, T. Heterocycles 1985, 23, 1629-1633. Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc., Chem. Comm. 1988, 509-510. Nagao, Y.; Dai, W.-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211-5217. Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393-412. Paolucci, C.; Venturelli, F.; Fava, A. Tetrahedron Lett. 1995, 36, 8127-8128. Liddell, J. R. Nat. Prod. Rep. 1996, 13, 187-193, and references cited therein.
122. (26) For other synthesis of the (+)-Geissman-Waiss lactone, as well as its applications in pyrrolizidine alkaloid syntheses, see: Shishido, K.; Sukegawa, Y.; Fukumoto, K.; Kametani, T. Heterocycles 1985, 23, 1629-1633. Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc., Chem. Comm. 1988, 509-510. Nagao, Y.; Dai, W.-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211-5217. Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393-412. Paolucci, C.; Venturelli, F.; Fava, A. Tetrahedron Lett. 1995, 36, 8127-8128. Liddell, J. R. Nat. Prod. Rep. 1996, 13, 187-193, and references cited therein.
123. (26) For other synthesis of the (+)-Geissman-Waiss lactone, as well as its applications in pyrrolizidine alkaloid syntheses, see: Shishido, K.; Sukegawa, Y.; Fukumoto, K.; Kametani, T. Heterocycles 1985, 23, 1629-1633. Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc., Chem. Comm. 1988, 509-510. Nagao, Y.; Dai, W.-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211-5217. Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393-412. Paolucci, C.; Venturelli, F.; Fava, A. Tetrahedron Lett. 1995, 36, 8127-8128. Liddell, J. R. Nat. Prod. Rep. 1996, 13, 187-193, and references cited therein.
124. (26) For other synthesis of the (+)-Geissman-Waiss lactone, as well as its applications in pyrrolizidine alkaloid syntheses, see: Shishido, K.; Sukegawa, Y.; Fukumoto, K.; Kametani, T. Heterocycles 1985, 23, 1629-1633. Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc., Chem. Comm. 1988, 509-510. Nagao, Y.; Dai, W.-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211-5217. Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393-412. Paolucci, C.; Venturelli, F.; Fava, A. Tetrahedron Lett. 1995, 36, 8127-8128. Liddell, J. R. Nat. Prod. Rep. 1996, 13, 187-193, and references cited therein.
125. (26) For other synthesis of the (+)-Geissman-Waiss lactone, as well as its applications in pyrrolizidine alkaloid syntheses, see: Shishido, K.; Sukegawa, Y.; Fukumoto, K.; Kametani, T. Heterocycles 1985, 23, 1629-1633. Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc., Chem. Comm. 1988, 509-510. Nagao, Y.; Dai, W.-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211-5217. Niwa, H.; Miyachi, Y.; Okamoto, O.; Uosaki, Y.; Kuroda, A.; Ishiwata, H.; Yamada, K. Tetrahedron 1992, 48, 393-412. Paolucci, C.; Venturelli, F.; Fava, A. Tetrahedron Lett. 1995, 36, 8127-8128. Liddell, J. R. Nat. Prod. Rep. 1996, 13, 187-193, and references cited therein.
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127. (28) Mallams, A. K. In Carbohydrate Chemistry; Kennedy, J. F., Ed.; Claredon Press: Oxford; 1988; pp 73-133. Carbohydrate Modifications in Antisense Research; Sanghvi, Y. S., Cook, P. D., Eds.; ACS Symposium Series 580; American Chemical Society: Washington; 1994. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677-1716.
128. (28) Mallams, A. K. In Carbohydrate Chemistry; Kennedy, J. F., Ed.; Claredon Press: Oxford; 1988; pp 73-133. Carbohydrate Modifications in Antisense Research; Sanghvi, Y. S., Cook, P. D., Eds.; ACS Symposium Series 580; American Chemical Society: Washington; 1994. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677-1716.
129. (28) Mallams, A. K. In Carbohydrate Chemistry; Kennedy, J. F., Ed.; Claredon Press: Oxford; 1988; pp 73-133. Carbohydrate Modifications in Antisense Research; Sanghvi, Y. S., Cook, P. D., Eds.; ACS Symposium Series 580; American Chemical Society: Washington; 1994. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677-1716.
130. (28) Mallams, A. K. In Carbohydrate Chemistry; Kennedy, J. F., Ed.; Claredon Press: Oxford; 1988; pp 73-133. Carbohydrate Modifications in Antisense Research; Sanghvi, Y. S., Cook, P. D., Eds.; ACS Symposium Series 580; American Chemical Society: Washington; 1994. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677-1716.
131. (29) Curtis, W. D.; Laidler, D. A.; Stoddart, J. F.; Jones, G. H. J. Chem. Soc., Perkin Trans. 1 1977, 1756-1769.
132. (30) At the outset of our work, Seebach, Ohno, and Haines, independiently, reported similar procedures for the synthesis of the benzylidene acetal of the esters of chiral tartaric acids; see: Hungerbühler, E.; Seebach, D.; Wasmuth, D. Helv. Chim. Acta 1981, 64, 1467-1487. Ohno, M.; Fujita, K.; Nakai, H.; Kobayashi, S.; Inoue, K.; Nojima, S. Chem. Pharm. Bull. 1985, 33, 572-582; Al-Hakim, A. H.; Haines, A. H.; Morley, C. Synthesis 1985, 207-208. For a recent synthesis of 17 from (R,R)-tartaric acid, see: Byun, H.-S.; Bittman, R. Synthetic Comm. 1993, 23, 3201-3204.
133. (30) At the outset of our work, Seebach, Ohno, and Haines, independiently, reported similar procedures for the synthesis of the benzylidene acetal of the esters of chiral tartaric acids; see: Hungerbühler, E.; Seebach, D.; Wasmuth, D. Helv. Chim. Acta 1981, 64, 1467-1487. Ohno, M.; Fujita, K.; Nakai, H.; Kobayashi, S.; Inoue, K.; Nojima, S. Chem. Pharm. Bull. 1985, 33, 572-582; Al-Hakim, A. H.; Haines, A. H.; Morley, C. Synthesis 1985, 207-208. For a recent synthesis of 17 from (R,R)-tartaric acid, see: Byun, H.-S.; Bittman, R. Synthetic Comm. 1993, 23, 3201-3204.
134. (30) At the outset of our work, Seebach, Ohno, and Haines, independiently, reported similar procedures for the synthesis of the benzylidene acetal of the esters of chiral tartaric acids; see: Hungerbühler, E.; Seebach, D.; Wasmuth, D. Helv. Chim. Acta 1981, 64, 1467-1487. Ohno, M.; Fujita, K.; Nakai, H.; Kobayashi, S.; Inoue, K.; Nojima, S. Chem. Pharm. Bull. 1985, 33, 572-582; Al-Hakim, A. H.; Haines, A. H.; Morley, C. Synthesis 1985, 207-208. For a recent synthesis of 17 from (R,R)-tartaric acid, see: Byun, H.-S.; Bittman, R. Synthetic Comm. 1993, 23, 3201-3204.
135. (30) At the outset of our work, Seebach, Ohno, and Haines, independiently, reported similar procedures for the synthesis of the benzylidene acetal of the esters of chiral tartaric acids; see: Hungerbühler, E.; Seebach, D.; Wasmuth, D. Helv. Chim. Acta 1981, 64, 1467-1487. Ohno, M.; Fujita, K.; Nakai, H.; Kobayashi, S.; Inoue, K.; Nojima, S. Chem. Pharm. Bull. 1985, 33, 572-582; Al-Hakim, A. H.; Haines, A. H.; Morley, C. Synthesis 1985, 207-208. For a recent synthesis of 17 from (R,R)-tartaric acid, see: Byun, H.-S.; Bittman, R. Synthetic Comm. 1993, 23, 3201-3204.
136. (31) We have found that, in general, the use of molecular sieves for removing water is more efficient than the Dean-Stark device in terms of higher yield and selectivity, as well as faster reactions and reproducibility when the reaction is scaled-up. For an earlier example, see: Herradón, B.; Seebach, D. Helv. Chim. Acta 1989, 72, 690-711. Herradón, B.; Arroyo, E.; Cueto, S.; Valverde, S.; unpublished results.
137. (31) We have found that, in general, the use of molecular sieves for removing water is more efficient than the Dean-Stark device in terms of higher yield and selectivity, as well as faster reactions and reproducibility when the reaction is scaled-up. For an earlier example, see: Herradón, B.; Seebach, D. Helv. Chim. Acta 1989, 72, 690-711. Herradón, B.; Arroyo, E.; Cueto, S.; Valverde, S.; unpublished results.
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140. (34) In our hand, the reductive opening of the benzylidene acetal by the method reported by Takano was less satisfactory, see: Takano, S.; Kurotaki, A.; Sekiguchi, Y.; Satoh, S.; Hirama, M.; Ogasawara, K. Synthesis 1986, 811-817.
141. (35) In our synthetic plan, both the 5-membered acetal 20 and the 6-membered acetal 21 are useful for the preparation of protected derivatives of (S,S)-5-hydroxy-6-hydroxymethyl-5,6-dihydro-2H-pyran-2-one, simply by changing the deprotection scheme, as indicated below. (formula presented)
142. (36) Greene, T. W.; Wuts, P. G. M. Protecting Groups in Organic Synthesis; John Wiley and Sons, Inc: New York; 1991; pp 123-127.
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146. 4-chiral building blocks 18 and 20, and their enantiomers, see: Toshima, H.; Yoshida, S.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6721-6724. Ito, M.; Kibayashi, M. Tetrahedron Lett. 1990, 31, 5065-5068. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Engli 1990, 29, 1169-1171. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 273-274. Carreaux, F.; Duréault, A.; Depezay, J. C. Synlett 1992, 527-529. Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201-4210. Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293-294. Pandey, G.; Ghorai, M. K.; Hajra, S. Pure Appl. Chem. 1996, 68, 653-658. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
147. 4-chiral building blocks 18 and 20, and their enantiomers, see: Toshima, H.; Yoshida, S.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6721-6724. Ito, M.; Kibayashi, M. Tetrahedron Lett. 1990, 31, 5065-5068. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Engli 1990, 29, 1169-1171. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 273-274. Carreaux, F.; Duréault, A.; Depezay, J. C. Synlett 1992, 527-529. Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201-4210. Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293-294. Pandey, G.; Ghorai, M. K.; Hajra, S. Pure Appl. Chem. 1996, 68, 653-658. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
148. 4-chiral building blocks 18 and 20, and their enantiomers, see: Toshima, H.; Yoshida, S.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6721-6724. Ito, M.; Kibayashi, M. Tetrahedron Lett. 1990, 31, 5065-5068. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Engli 1990, 29, 1169-1171. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 273-274. Carreaux, F.; Duréault, A.; Depezay, J. C. Synlett 1992, 527-529. Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201-4210. Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293-294. Pandey, G.; Ghorai, M. K.; Hajra, S. Pure Appl. Chem. 1996, 68, 653-658. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
149. 4-chiral building blocks 18 and 20, and their enantiomers, see: Toshima, H.; Yoshida, S.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6721-6724. Ito, M.; Kibayashi, M. Tetrahedron Lett. 1990, 31, 5065-5068. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Engli 1990, 29, 1169-1171. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 273-274. Carreaux, F.; Duréault, A.; Depezay, J. C. Synlett 1992, 527-529. Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201-4210. Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293-294. Pandey, G.; Ghorai, M. K.; Hajra, S. Pure Appl. Chem. 1996, 68, 653-658. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
150. 4-chiral building blocks 18 and 20, and their enantiomers, see: Toshima, H.; Yoshida, S.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6721-6724. Ito, M.; Kibayashi, M. Tetrahedron Lett. 1990, 31, 5065-5068. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Engli 1990, 29, 1169-1171. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 273-274. Carreaux, F.; Duréault, A.; Depezay, J. C. Synlett 1992, 527-529. Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201-4210. Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293-294. Pandey, G.; Ghorai, M. K.; Hajra, S. Pure Appl. Chem. 1996, 68, 653-658. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
151. 4-chiral building blocks 18 and 20, and their enantiomers, see: Toshima, H.; Yoshida, S.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6721-6724. Ito, M.; Kibayashi, M. Tetrahedron Lett. 1990, 31, 5065-5068. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Engli 1990, 29, 1169-1171. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 273-274. Carreaux, F.; Duréault, A.; Depezay, J. C. Synlett 1992, 527-529. Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201-4210. Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293-294. Pandey, G.; Ghorai, M. K.; Hajra, S. Pure Appl. Chem. 1996, 68, 653-658. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
152. 4-chiral building blocks 18 and 20, and their enantiomers, see: Toshima, H.; Yoshida, S.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6721-6724. Ito, M.; Kibayashi, M. Tetrahedron Lett. 1990, 31, 5065-5068. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Engli 1990, 29, 1169-1171. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 273-274. Carreaux, F.; Duréault, A.; Depezay, J. C. Synlett 1992, 527-529. Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201-4210. Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293-294. Pandey, G.; Ghorai, M. K.; Hajra, S. Pure Appl. Chem. 1996, 68, 653-658. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
153. 4-chiral building blocks 18 and 20, and their enantiomers, see: Toshima, H.; Yoshida, S.; Suzuki, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6721-6724. Ito, M.; Kibayashi, M. Tetrahedron Lett. 1990, 31, 5065-5068. Wehner, V.; Jäger, V. Angew. Chem. Int. Ed. Engli 1990, 29, 1169-1171. Ghosh, A. K.; McKee, S. P.; Lee, H. Y.; Thompson, W. J. J. Chem. Soc., Chem. Commun. 1992, 273-274. Carreaux, F.; Duréault, A.; Depezay, J. C. Synlett 1992, 527-529. Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201-4210. Lee, E.; Park, C. M. J. Chem. Soc., Chem. Commun. 1994, 293-294. Pandey, G.; Ghorai, M. K.; Hajra, S. Pure Appl. Chem. 1996, 68, 653-658. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475-3478.
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160. (b) Reaction with thioanisole/N-chlorosuccinimide (Fraser-Reid, B.; Molino, B. F.; Magdzinski, L.; Mootoo, D. R. J. Org. Chem. 1987, 52, 4505-4511).
161. (46) In general alkoxy aldehydes are relatively unstable and hydratable; for some examples, see: Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265-276. Mukai, C.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1993, 34, 6081-6082. Takebuchi, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 5239-5242.
162. (46) In general alkoxy aldehydes are relatively unstable and hydratable; for some examples, see: Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265-276. Mukai, C.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1993, 34, 6081-6082. Takebuchi, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 5239-5242.
163. (46) In general alkoxy aldehydes are relatively unstable and hydratable; for some examples, see: Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265-276. Mukai, C.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1993, 34, 6081-6082. Takebuchi, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 5239-5242.
164. 3, 50.3 MHz) δ 189.1 (d), 138.2 (d), 136.5 (s), 128.5 (s), 127.9 (d, 3C), 127.8 (d, 2C), 73.0 (t), 57.4 (t).
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166. 2O, 2H).
167. (50) Analougosly to the synthesis of (+)-5, the preparation of 31, bearing a more labile protecting group, was tried. Although the α,β-unsaturated ester 32 was uneventfully prepared from either (R,R)-dimethyl tartrate or (R,R)-diethyl tartrate, we were unable to selectively deblock the terminal glycol unity without affecting the p-methoxybenzyloxy group [Bao, R.; Herradón, B.; unpublished observations] (formula presented)
168. (51) Herradón, B.; Bao, R.; Fenude, E.; Valverde, S. J. Org. Chem. 1996, 61, 1143-1147.
169. (52) For recent syntheses of L-sugars, see: Llera, J.-M.; Trujillo, M.; Blanco, M.-E.; Alcudia, F. Tetrahedron: Asymmetry 1994, 5, 709-716. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311-4312. Giuliano, R. M.; Villani, Jr., F. J. J. Org. Chem. 1995, 60, 202-211. Davies, S. G.; Smyth, G. D. Tetrahedron: Asymmetry 1996, 7, 1273-1274. For recent syntheses of branched-chain sugars, see: Yanagihara, R.; Osanai, S.; Yoshikawa, S. Chem. Lett. 1992, 89-90. Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061-4069.
170. (52) For recent syntheses of L-sugars, see: Llera, J.-M.; Trujillo, M.; Blanco, M.-E.; Alcudia, F. Tetrahedron: Asymmetry 1994, 5, 709-716. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311-4312. Giuliano, R. M.; Villani, Jr., F. J. J. Org. Chem. 1995, 60, 202-211. Davies, S. G.; Smyth, G. D. Tetrahedron: Asymmetry 1996, 7, 1273-1274. For recent syntheses of branched-chain sugars, see: Yanagihara, R.; Osanai, S.; Yoshikawa, S. Chem. Lett. 1992, 89-90. Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061-4069.
171. (52) For recent syntheses of L-sugars, see: Llera, J.-M.; Trujillo, M.; Blanco, M.-E.; Alcudia, F. Tetrahedron: Asymmetry 1994, 5, 709-716. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311-4312. Giuliano, R. M.; Villani, Jr., F. J. J. Org. Chem. 1995, 60, 202-211. Davies, S. G.; Smyth, G. D. Tetrahedron: Asymmetry 1996, 7, 1273-1274. For recent syntheses of branched-chain sugars, see: Yanagihara, R.; Osanai, S.; Yoshikawa, S. Chem. Lett. 1992, 89-90. Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061-4069.
172. (52) For recent syntheses of L-sugars, see: Llera, J.-M.; Trujillo, M.; Blanco, M.-E.; Alcudia, F. Tetrahedron: Asymmetry 1994, 5, 709-716. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311-4312. Giuliano, R. M.; Villani, Jr., F. J. J. Org. Chem. 1995, 60, 202-211. Davies, S. G.; Smyth, G. D. Tetrahedron: Asymmetry 1996, 7, 1273-1274. For recent syntheses of branched-chain sugars, see: Yanagihara, R.; Osanai, S.; Yoshikawa, S. Chem. Lett. 1992, 89-90. Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061-4069.
173. (52) For recent syntheses of L-sugars, see: Llera, J.-M.; Trujillo, M.; Blanco, M.-E.; Alcudia, F. Tetrahedron: Asymmetry 1994, 5, 709-716. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311-4312. Giuliano, R. M.; Villani, Jr., F. J. J. Org. Chem. 1995, 60, 202-211. Davies, S. G.; Smyth, G. D. Tetrahedron: Asymmetry 1996, 7, 1273-1274. For recent syntheses of branched-chain sugars, see: Yanagihara, R.; Osanai, S.; Yoshikawa, S. Chem. Lett. 1992, 89-90. Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061-4069.
174. (52) For recent syntheses of L-sugars, see: Llera, J.-M.; Trujillo, M.; Blanco, M.-E.; Alcudia, F. Tetrahedron: Asymmetry 1994, 5, 709-716. Pepito, A. S.; Dittmer, D. C. J. Org. Chem. 1994, 59, 4311-4312. Giuliano, R. M.; Villani, Jr., F. J. J. Org. Chem. 1995, 60, 202-211. Davies, S. G.; Smyth, G. D. Tetrahedron: Asymmetry 1996, 7, 1273-1274. For recent syntheses of branched-chain sugars, see: Yanagihara, R.; Osanai, S.; Yoshikawa, S. Chem. Lett. 1992, 89-90. Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061-4069.
175. 2O, 1H).
176. (54) (a) Sánchez-Sancho, F.; Herradón, B.; work in progress,
177. (b) On the contrary, the intermolecular Michael addition of oxygen-nucleophiles goes with poor stereocontrol, probably due to partial epimerization of the initially formed product through a retro-Michael addition [Herradón, B. Ph. D. Dissertation, Universidad Complutense, Madrid, 1986. García-Ochoa, S. Ph D. Dissertation, Universidad Autonoma, Madrid, 1988].
178. (b) On the contrary, the intermolecular Michael addition of oxygen-nucleophiles goes with poor stereocontrol, probably due to partial epimerization of the initially formed product through a retro-Michael addition [Herradón, B. Ph. D. Dissertation, Universidad Complutense, Madrid, 1986. García-Ochoa, S. Ph D. Dissertation, Universidad Autonoma, Madrid, 1988].
179. (c) For recent stereocontrolled synthesis of chiral tetrahydrofurans, see: Bertrand, P. B.; Gesson, J.-P.; Renoux, B.; Tranoy, I. Tetrahedron Lett. 1995, 36, 4073-4076. Bratt, K.; Garavelas, A.; Perlmutter, P.; Westman, G. J. Org. Chem. 1996, 61, 2109-2117.
180. (c) For recent stereocontrolled synthesis of chiral tetrahydrofurans, see: Bertrand, P. B.; Gesson, J.-P.; Renoux, B.; Tranoy, I. Tetrahedron Lett. 1995, 36, 4073-4076. Bratt, K.; Garavelas, A.; Perlmutter, P.; Westman, G. J. Org. Chem. 1996, 61, 2109-2117.
181. (d) For a recent review on the intramolecular Michael addition, see: Little, R. D.; Masjedizadeh, M. R.; Wallquist, O.; McLoughlin, J. I. Organic Reactions 1995, 47, 315-552.
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185. (58) (a) We are studying the possibility to transform the diol 41, and related compounds, to monoacyl derivatives, such as 11, by an enzymatic method; for a related procedure, see: Herradón, B.; Valverde, S. Synlett 1995, 599-602.
186. (b) We have recently found that the acylase I from Aspergillus species catalyzes the benzoylation of alcohols using vinyl benzoate as acylating agent (Herradón, B.; Faraldos, J.; Arroyo, E.; unpublished results).
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190. (61) (a) The acetal 49 was previously prepared in 8 steps from (R,R)-dimethyl tartrate, see: Hungerbühler, E.; Seebach, D.; Wasmuth, D. Angew. Chem. Int. Ed. Engl. 1979, 18, 958-960.
191. (b) Compound 49 and its enantiomer have been synthesized by a chemo-enzymatic approach, see: Herradón, B.; Valverde, S. Tetrahedron: Asymmetry 1994, 5, 1479-1500.
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219. (78) The fact that these lactones are quite conformationally mobile and show quite long relaxation times, made difficult to observe strong NOEs. We thank Prof. M. Bernabé for helpful hints regarding this point.
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223. 6 solution.
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225. (84) The enantiomer of the dibenzoate 42 has been described, see: Georges, M.; MacKay, D.; Fraser-Reid, B. Can. J. Chem. 1984, 62, 1539-1543.
226. 27,70
227. (86) Financial support from DGICYT (Project numbers PB-93-0154 and PB-94-0104) is gratefully acknowledged.