Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond formations

Journal of the American Chemical Society

Volumn 119, Issue 39, 1997, Pages 9130-9136

  Fürstner, Alois ^a   Langemann, Klaus ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GLOEOSPORONE; MACROLIDE; RICINELAIDOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0038163433     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9719945     Document Type: Article

References (77)

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9. For general reviews on olefin metathesis in organic synthesis, see the following for leading references: (a) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: New York, 1997. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (c) Fürstner, A. Topics in Catalysis In press.
10. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
11. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
12. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
13. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
14. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
15. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
16. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
17. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
18. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
19. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
20. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
21. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
22. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
23. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
24. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
25. For other examples of macrocyclization reactions via RCM using various catalysts, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 3191. (b) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855. (c) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606. (d) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364. (e) König, B.; Horn, C. Synlett 1996, 1013. (f) McKervey, M. A.; Pitarch, M. J. Chem. Soc., Chem. Commun. 1996, 1689. (g) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. 1997, 109, 170. (h) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554. (i) Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M.; Cordes, M. Angew. Chem. 1997, 109, 543. (j) Bertiano, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000. (k) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943. (l) Martin, S. F.; Liao, Y.; Chen, H.-J.; Pätzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 6005. (m) Tsuji, J.; Hashiguchi, S. Tetrahedron Lett. 1980, 2955. (n) Villemin, D. Tetrahedron Lett. 1980, 1715. (o) Plugge, M. F. C.; Mol, J. C. Synlett 1991, 507. (p) Descotes, G.; Ramza, J.; Basset, J.-M.; Pagano, S.; Gentil, E.; Banoub, J. Tetrahedron 1996, 52, 10903.
26. For the preparation of the ruthenium carbenes 1a,b, see: (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974. (c) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179. (d) For the preparation of 2, see: Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
27. For the preparation of the ruthenium carbenes 1a,b, see: (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974. (c) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179. (d) For the preparation of 2, see: Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
28. For the preparation of the ruthenium carbenes 1a,b, see: (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974. (c) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179. (d) For the preparation of 2, see: Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
29. For the preparation of the ruthenium carbenes 1a,b, see: (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974. (c) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179. (d) For the preparation of 2, see: Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
30. Trost, B. M. Angew. Chem. 1995, 107, 285.
31. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
32. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
33. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
34. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
35. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
36. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
37. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
38. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
39. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
40. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
41. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
42. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
43. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
44. For previous syntheses, see: (a) Thalmann, A.; Oertle, K.; Gerlach, H. Org. Synth. 1990, 63, 192. (b) Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755. (c) Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem., Int. Ed. Engl. 1977, 16, 876. (d) Narasaka, K.; Yamaguchi, M.; Mukaiyama, T. Chem. Lett. 1977, 959. (e) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989. (f) Venkataraman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1893. (g) Kruizinga, W. H.; Kellog, R. M. J. Am. Chem. Soc. 1981, 103, 5183. (h) Regen, S. L.; Kimura, Y. J. Am. Chem. Soc. 1982, 104, 2064. (i) Steliou, K.; Poupart, M.-A. J. Am. Chem. Soc. 1983, 105, 7130. (j) Ahmed, A.; Taniguchi, N.; Fukuda, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781. (k) Gais, H. J. Tetrahedron Lett. 1984, 25, 273. (l) Shono, T.; Ishige, O.; Uyama, H.; Kashimura, S. J. Org. Chem. 1986, 51, 546. (m) Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501. (n) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
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