SmI2 in a 6-exo-dig radical cyclisation in a synthetic approach to (±)-erigerol

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5523-5526

  Anies, Claude ^a   Lallemand, Jean Yves ^a   Pancrazi, Ange ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FORSKOLIN; TERPENOID;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01187-2     Document Type: Article

References (42)

1. (1) Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J.; Fehlhaber, H.-W. Tetrahedron Lett. 1977, 1669-72. Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J. J. Chem. Soc. Perkin Trans 1 1982, 767-71.
2. (1) Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J.; Fehlhaber, H.-W. Tetrahedron Lett. 1977, 1669-72. Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J. J. Chem. Soc. Perkin Trans 1 1982, 767-71.
3. (2) Anies, C.; Pancrazi, A.; Lallemand, J.Y. Tetrahedron Lett. 1995, 36, 2075-78.
4. (3) Anies, C.; Billot, L.; Lallemand, J.Y.; Pancrazi, A. Tetrahedron Lett. 1995, 36, 7247-50.
5. (4) Total synthesis of erigerol: Kienzle, F.; Stadlwieser, J.; Rank, W.; Mergelsberg, I. Tetrahedron Lett. 1988, 29, 6479-82. Kienzle, F.; Stadlwieser, J.; Rank, W.; Schönholzer, P. Helv. Chim. Acta 1990, 73, 1108-38 .
6. (4) Total synthesis of erigerol: Kienzle, F.; Stadlwieser, J.; Rank, W.; Mergelsberg, I. Tetrahedron Lett. 1988, 29, 6479-82. Kienzle, F.; Stadlwieser, J.; Rank, W.; Schönholzer, P. Helv. Chim. Acta 1990, 73, 1108-38 .
7. Synthetic approaches: a) Colombo, M. I.; Zinczuk, J.; Bacigaluppo, J. A.; Somoza, C.; Ruveda, E. A. J. Org. Chem. 1990, 55, 5631-39 and references cited therein.
8. b) Preite, M. D. ; Ruveda, E. A. Synth. Commun. 1994, 24, 2809-25.
9. (5) For total synthesis of forskolin see: -a) Ziegler, F. E.; Jaynes, B. H.; Saindane, M. T. Tetrahedron Lett. 1985, 26, 3307-10. Ziegler, F. E.; Jaynes, B. H.; Saindane, M. T. J. Am. Chem. Soc. 1987, 109, 8115-16.
10. (5) For total synthesis of forskolin see: -a) Ziegler, F. E.; Jaynes, B. H.; Saindane, M. T. Tetrahedron Lett. 1985, 26, 3307-10. Ziegler, F. E.; Jaynes, B. H.; Saindane, M. T. J. Am. Chem. Soc. 1987, 109, 8115-16.
11. -b) Hashimoto, S.; Sakata, S.; Sonegawa, M.; Ikegami, S., J. Am. Chem. Soc. 1988, 110, 3670-72.
12. -c) Corey, E. J.; Da Silva Jardine, P; Rohloff, J. C. J. Am. Chem. Soc. 1988, 110, 3672-73. Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409-12. Corey, E. J.; Da Silva Jardine, P. Tetrahedron Lett. 1989, 30, 7297-300.
13. -c) Corey, E. J.; Da Silva Jardine, P; Rohloff, J. C. J. Am. Chem. Soc. 1988, 110, 3672-73. Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409-12. Corey, E. J.; Da Silva Jardine, P. Tetrahedron Lett. 1989, 30, 7297-300.
14. -c) Corey, E. J.; Da Silva Jardine, P; Rohloff, J. C. J. Am. Chem. Soc. 1988, 110, 3672-73. Corey, E. J.; Da Silva Jardine, P.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409-12. Corey, E. J.; Da Silva Jardine, P. Tetrahedron Lett. 1989, 30, 7297-300.
15. -d) Delpech, B.; Calvo, D.; Lett, R. Tetrahedron Lett. 1996, 37, 1015-18. ibid 1996, 37, 1019-22. Calvo, D.; Port, M.; Delpech, B.; Lett, R. Tetrahedron Lett. 1996, 37, 1023-24. For a review see: Colombo, M. I.; Zinczuk, J.; Ruveda, E. A. Tetrahedron, 1992, 48, 963-1037, and references cited therein. For a recent formal synthesis of forskolin see ref 2.
16. -d) Delpech, B.; Calvo, D.; Lett, R. Tetrahedron Lett. 1996, 37, 1015-18. ibid 1996, 37, 1019-22. Calvo, D.; Port, M.; Delpech, B.; Lett, R. Tetrahedron Lett. 1996, 37, 1023-24. For a review see: Colombo, M. I.; Zinczuk, J.; Ruveda, E. A. Tetrahedron, 1992, 48, 963-1037, and references cited therein. For a recent formal synthesis of forskolin see ref 2.
17. -d) Delpech, B.; Calvo, D.; Lett, R. Tetrahedron Lett. 1996, 37, 1015-18. ibid 1996, 37, 1019-22. Calvo, D.; Port, M.; Delpech, B.; Lett, R. Tetrahedron Lett. 1996, 37, 1023-24. For a review see: Colombo, M. I.; Zinczuk, J.; Ruveda, E. A. Tetrahedron, 1992, 48, 963-1037, and references cited therein. For a recent formal synthesis of forskolin see ref 2.
18. -d) Delpech, B.; Calvo, D.; Lett, R. Tetrahedron Lett. 1996, 37, 1015-18. ibid 1996, 37, 1019-22. Calvo, D.; Port, M.; Delpech, B.; Lett, R. Tetrahedron Lett. 1996, 37, 1023-24. For a review see: Colombo, M. I.; Zinczuk, J.; Ruveda, E. A. Tetrahedron, 1992, 48, 963-1037, and references cited therein. For a recent formal synthesis of forskolin see ref 2.
19. (6) Anies, C.; Pancrazi, A.; Lallemand, J.-Y.; Prange, T. Tetrahedron Lett. 1994, 35, 7771-72.
20. (7) Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 2647-50.
21. (8) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Ishiguro, M.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1029-30. See also Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 5041-43. Corey, E. J.; Terashima, S. Tetrahedron Lett. 1972, 1815-16. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. For an asymetric aldol reaction using a propargylic titanium reagent and (-)-sparteine see Dieller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400. For reaction with allenic zincate see Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24.
22. (8) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Ishiguro, M.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1029-30. See also Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 5041-43. Corey, E. J.; Terashima, S. Tetrahedron Lett. 1972, 1815-16. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. For an asymetric aldol reaction using a propargylic titanium reagent and (-)-sparteine see Dieller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400. For reaction with allenic zincate see Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24.
23. (8) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Ishiguro, M.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1029-30. See also Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 5041-43. Corey, E. J.; Terashima, S. Tetrahedron Lett. 1972, 1815-16. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. For an asymetric aldol reaction using a propargylic titanium reagent and (-)-sparteine see Dieller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400. For reaction with allenic zincate see Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24.
24. (8) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Ishiguro, M.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1029-30. See also Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 5041-43. Corey, E. J.; Terashima, S. Tetrahedron Lett. 1972, 1815-16. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. For an asymetric aldol reaction using a propargylic titanium reagent and (-)-sparteine see Dieller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400. For reaction with allenic zincate see Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24.
25. (8) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Ishiguro, M.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1029-30. See also Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 5041-43. Corey, E. J.; Terashima, S. Tetrahedron Lett. 1972, 1815-16. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. For an asymetric aldol reaction using a propargylic titanium reagent and (-)-sparteine see Dieller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400. For reaction with allenic zincate see Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24.
26. (8) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Ishiguro, M.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1029-30. See also Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 5041-43. Corey, E. J.; Terashima, S. Tetrahedron Lett. 1972, 1815-16. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. For an asymetric aldol reaction using a propargylic titanium reagent and (-)-sparteine see Dieller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400. For reaction with allenic zincate see Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24.
27. (8) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Ishiguro, M.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1029-30. See also Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 5041-43. Corey, E. J.; Terashima, S. Tetrahedron Lett. 1972, 1815-16. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. For an asymetric aldol reaction using a propargylic titanium reagent and (-)-sparteine see Dieller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400. For reaction with allenic zincate see Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24.
28. (8) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Ishiguro, M.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1029-30. See also Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 5041-43. Corey, E. J.; Terashima, S. Tetrahedron Lett. 1972, 1815-16. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. For an asymetric aldol reaction using a propargylic titanium reagent and (-)-sparteine see Dieller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400. For reaction with allenic zincate see Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24.
29. (9) Anies, C.; Lallemaand, J.-Y.; Pancrazi, A. Tetrahedron Lett., accompanying note.
30. 2-O), 218.2 (C=O, C-9).
31. (11) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc 1980, 102, 2693-98. Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765-66. Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-66. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-61.
32. (11) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc 1980, 102, 2693-98. Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765-66. Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-66. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-61.
33. (11) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc 1980, 102, 2693-98. Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765-66. Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-66. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-61.
34. (11) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc 1980, 102, 2693-98. Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765-66. Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-66. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-61.
35. 3)], 151.9 (C-8).
36. (13) Molander, G. A.; McKie, J. A. J. Org. Chem 1995, 60, 872-82. For a review see also, Molander, G. A. Chem Rev 1992, 92, 29-68.
37. (13) Molander, G. A.; McKie, J. A. J. Org. Chem 1995, 60, 872-82. For a review see also, Molander, G. A. Chem Rev 1992, 92, 29-68.
38. (14) Shim, S. C.; Hwang, J. T.; Kang, H.-Y.; Chang, M. H. Tetrahedron Lett. 1990, 31, 4765-68.
39. 2-O), 115.5 (C-11), 214.7 (C=O, C-9).
40. (16) Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061-69.
41. (17) Hanessian, S.; Girard, C.; Chiara, J. L. Tetrahedron Lett. 1992, 33, 573-76.
42. (18) Magid, R. M. Tetrahedron 1980, 36, 1901-30.