Novel anionic polycyclisation cascade. Highly stereocontrolled assembly of functionalised tetracycles akin to the middle core of the manzamines

Tetrahedron Letters

Volumn 43, Issue 37, 2002, Pages 6591-6595

  Turet, Laurent ^a   Markó, István E ^a   Tinant, Bernard ^a   Declercq, Jean Paul ^a   Touillaux, Rolland ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

keto phosphonates; Anionic polycyclisation; Manzamines; Perhydroisoquinoline; Stereocontrol

Indexed keywords

ACROLEIN; MANZAMINE A; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; DRUG TRANSFORMATION; HORNER WADSWORTH EMMONS REACTION; MICHAEL ADDITION; POLYMERIZATION; REACTION TIME; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0037048469     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01463-6     Document Type: Article

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33. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
34. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
35. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
36. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
37. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
38. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
39. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
40. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
41. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
42. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
43. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
44. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
45. For some selected examples of anionic cyclisations, see: (a) Danishefsky, S.; Hatch, W. E.; Sax, M.; Abola, E.; Pletcher, J. J. Am. Chem. Soc. 1973, 95, 2410; (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310; (c) Ihara, M.; Toyota, M.; Fukumoto, K.; Kametami, T. Tetrahedron Lett. 1984, 25, 2167; (d) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010; (e) Posner, G. H.; Asirvatham, E. Tetrahedron Lett. 1986, 27, 663; (f) Braun, N. A.; Klein, I.; Spitzner, D.; Vogel, B.; Borrmann, H.; Simon, A. Tetrahedron Lett. 1995, 36, 3675; (g) Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775; (h) Leclaire, M.; Levet, R.; Lallemand, J.-Y. Synth. Commun. 1993, 23, 1923; (i) Boons, G.-J.; Lennon, I. C.; Ley, S. V.; Owen, E. S. E.; Staunton, J.; Wadsworth, D. J. Tetrahedron Lett. 1994, 35, 323; (j) Lavoisier-Gallo, T.; Charonnet, E.; Rodroguez, J. J. Org. Chem. 1998, 63, 900; (k) Gutke, H.-J.; Oesterreich, K.; Spitzner, D.; Braun, N. A. Tetrahedron 2001, 57, 997. For reviews, see: (l) Tietze, L.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (m) Tietze, L. Chem. Rev. 1996, 96, 115.
46. Mortreux A., Blanchard A. J. Chem. Soc., Chem. Commun. 1974;786.
47. Fürstner A., Seidel G. Angew. Chem., Int. Ed. 37:1998;1734.
48. Proton exchange could occur either by direct deprotonation of 8 by 27 or by transfer from 27 to tBuOH.
49. 2: C, 77.48; H, 8.19. Found: C, 77.73; H, 8.21.