Highly stereoselective first synthesis of an A-ring-functionalized bakkane: Novel free-radical approach to 9-acetoxyfukinanolide

Journal of the American Chemical Society

Volumn 118, Issue 41, 1996, Pages 9992-9993

  Hamelin, Olivier ^a   Deprés, Jean Pierre ^a   Greene, Andrew E ^a   Tinant, Bernard ^b   Declercq, Jean Paul ^b  

^a UNIV GRENOBLE ALPES   (France)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

SESQUITERPENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029859436     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962517+     Document Type: Article

References (42)

1. (a) Abe. N.; Onoda. R.; Shirahata, K.; Kato, T.; Woods. M. C.; Kitahara, Y. Tetrahedron Lett. 1968. 9, 369-373.
2. (b) Abe, N.; Onoda. R.; Shirahata, K.; Kato, T.; Woods, M. C.; Kitahara, Y.; Ro, K.; Kurihara, T. Tetrahedron Lett. 1968. 9, 1993-1997.
3. (c) Shirahata, K.; Abe, N.; Kato, T.; Kitahara, Y. Bull. Chem. Soc. Jpn. 1968, 41, 1732-1733.
4. (d) Naya, K.; Takagi, I.; Hayashi, M.; Nakamura, S.; Kobayashi, M.; Katsumura, S. Chem. Ind. (London) 1968, 318-320.
5. (e) Shirahata, K.; Kato, T.; Kitahara, Y.; Abe, N. Tetrahedron 1969, 25, 3179-3191; 4671-4680.
6. (f) Naya, K.; Hayashi, M.; Takagi, I.; Nakamura, S.; Kobayashi, M. Bull. Chem. Soc. Jpn. 1972, 45, 3673-3685.
7. (g) Naya, K.; Kawai, M.; Naito, M.; Kasai, T. Chem. Lett. 1972. 241-244.
8. (h) Harmatha, J.; Samek, Z.; Synackova, M.; Novotny, L.; Herout, V.; Sorm, F. Collect. Czech. Chem. Commun. 1976, 41, 2047-2058.
9. (i) Jakupovic, J.; Grenz, M.; Bohlmann, F. Planta Med. 1989, 55, 571-572.
10. (j) Wiemer, D. F.; Wolfe, L. K.; Fenical, W.: Strobel, S. A.; Clardy, J. Tetrahedron Lett. 1990, 31, 1973-1976.
11. Jamieson, G. R.; Reid, E. H.; Turner, B. P.; Jamieson, A. T. Phytochemistry 1976, 15, 1713-1715. Kano, K.; Hayashi, K.; Mitsuhashi, H.Chem. Pharm. Bull. 1982, 30, 1198-1203. Nawrot, J.; Bloszyk, E.; Harmatha, J.; Novotny, L.; Drozdz, B. Acta Entomol. Bohemoslov. 1986. 83, 327-335. Nawrot, J.; Harmatha, J.; Bloszyk, E. International Conference on Stored-Product Protection, 4th; Tel-Aviv, Sept. 1986.
12. Jamieson, G. R.; Reid, E. H.; Turner, B. P.; Jamieson, A. T. Phytochemistry 1976, 15, 1713-1715. Kano, K.; Hayashi, K.; Mitsuhashi, H.Chem. Pharm. Bull. 1982, 30, 1198-1203. Nawrot, J.; Bloszyk, E.; Harmatha, J.; Novotny, L.; Drozdz, B. Acta Entomol. Bohemoslov. 1986. 83, 327-335. Nawrot, J.; Harmatha, J.; Bloszyk, E. International Conference on Stored-Product Protection, 4th; Tel-Aviv, Sept. 1986.
13. Jamieson, G. R.; Reid, E. H.; Turner, B. P.; Jamieson, A. T. Phytochemistry 1976, 15, 1713-1715. Kano, K.; Hayashi, K.; Mitsuhashi, H.Chem. Pharm. Bull. 1982, 30, 1198-1203. Nawrot, J.; Bloszyk, E.; Harmatha, J.; Novotny, L.; Drozdz, B. Acta Entomol. Bohemoslov. 1986. 83, 327-335. Nawrot, J.; Harmatha, J.; Bloszyk, E. International Conference on Stored-Product Protection, 4th; Tel-Aviv, Sept. 1986.
14. Jamieson, G. R.; Reid, E. H.; Turner, B. P.; Jamieson, A. T. Phytochemistry 1976, 15, 1713-1715. Kano, K.; Hayashi, K.; Mitsuhashi, H.Chem. Pharm. Bull. 1982, 30, 1198-1203. Nawrot, J.; Bloszyk, E.; Harmatha, J.; Novotny, L.; Drozdz, B. Acta Entomol. Bohemoslov. 1986. 83, 327-335. Nawrot, J.; Harmatha, J.; Bloszyk, E. International Conference on Stored-Product Protection, 4th; Tel-Aviv, Sept. 1986.
15. (a) Hayashi, K.: Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
16. (b) Evans, D. A.; Sims, C. L.; Andrews, G. C. J. Am. Chem. Soc. 1977, 99, 5453-5461.
17. (c) Greene, A. E.; Deprés, J.-P.; Coelho, F.; Brocksom, T. J. J. Org. Chem. 1985, 50, 3943-3945.
18. (d) Greene, A. E.; Coelho, F.; Deprés, J.-P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662.
19. (e) Srikrishna, A.; Reddy, T. J.; Nagaraju, S.; Sattigeri,. J. A. Tetrahedron Lett. 1994, 35, 7841-7844.
20. (a) Hartmann, B.; Kanazawa, A. M.: Deprés, J.-P.; Greene, A. E. Tetrahedron Lett. 1991, 32, 767-768.
21. (b) Hartmann, B.; Kanazawa, A. M.; Deprés, J.-P.; Greene, A. E. Tetrahedron Lett. 1993, 34, 3875-3876.
22. (c) Mori, K.; Matsushima, Y. Synthesis 1995, 845-850.
23. (d) Srikrishna, A.; Reddy, T. J. Ind. J. Chem. 1995, 34B, 844-846.
24. (a) Coelho, F.; Deprés, J.-P.; Brocksom, T. J.; Greene, A. E. Tetrahedron Lett. 1989, 30, 565-566.
25. (b) Srikrishna, A.; Nagaraju, S.; Venkateswarlu. S. Tetrahedron Lett. 1994, 35, 429-432.
26. Hartmann, B.; Deprés. J.-P.; Greene. A. E.; Freire de Lima, M. E. Tetrahedron Lett. 1993, 34, 1487-1490.
27. 4: C, 69.83; H, 8.27. Found: C, 69.80: H, 8.11.
28. Liu, H. J.; Ogino, T. Tetrahedron Lett. 1973, 35, 4937-4940.
29. Snider, B. B. Chem. Rev. 1996, 96. 339-363 and references cited therein. For related, but less efficient, recent protocols for effecting freeradical spiro lactonization, see: ref 4d. Back, G. B.; Gladstone, P. L.; Parvez, M. J. Org. Chem. 1996, 61, 3806-3814. Also see: Clive, D. L. J.; Tao, Y.; Khodabocus. A.; Wu. Y.-J.; Angoh, A. G.; Bennett, S. M.; Boddy, C. N.; Bordeleau, L.; Keller, D.; Kleiner, G.; Middleton, D. S.; Nichols, C. J.; Richardson, S. R.; Vernon, P. G. J. Am. Chem. Soc: 1994, 116, 11275-11286. The generality of this β-methylene-γ-butyrolactonization is currently being studied in our laboratory.
30. Snider, B. B. Chem. Rev. 1996, 96. 339-363 and references cited therein. For related, but less efficient, recent protocols for effecting freeradical spiro lactonization, see: ref 4d. Back, G. B.; Gladstone, P. L.; Parvez, M. J. Org. Chem. 1996, 61, 3806-3814. Also see: Clive, D. L. J.; Tao, Y.; Khodabocus. A.; Wu. Y.-J.; Angoh, A. G.; Bennett, S. M.; Boddy, C. N.; Bordeleau, L.; Keller, D.; Kleiner, G.; Middleton, D. S.; Nichols, C. J.; Richardson, S. R.; Vernon, P. G. J. Am. Chem. Soc: 1994, 116, 11275-11286. The generality of this β-methylene-γ-butyrolactonization is currently being studied in our laboratory.
31. Snider, B. B. Chem. Rev. 1996, 96. 339-363 and references cited therein. For related, but less efficient, recent protocols for effecting freeradical spiro lactonization, see: ref 4d. Back, G. B.; Gladstone, P. L.; Parvez, M. J. Org. Chem. 1996, 61, 3806-3814. Also see: Clive, D. L. J.; Tao, Y.; Khodabocus. A.; Wu. Y.-J.; Angoh, A. G.; Bennett, S. M.; Boddy, C. N.; Bordeleau, L.; Keller, D.; Kleiner, G.; Middleton, D. S.; Nichols, C. J.; Richardson, S. R.; Vernon, P. G. J. Am. Chem. Soc: 1994, 116, 11275-11286. The generality of this β-methylene-γ-butyrolactonization is currently being studied in our laboratory.
32. Examination of the transition states leading to the two diastereomeric lactones was not sufficiently helpful to permit a confident assignment of the C-7 configuration.
33. For reviews, see: Molander, G. A. Org. React. 1994, 46, 211-367. Molander, G. A. Chem. Rev. 1992, 92, 29-68. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. For a similar reduction problem and an alternative solution, see: Wang, T.-Z.; Pinard, E.; Paquette, L. A. J. Am. Chem. Soc. 1996, 778, 1309-1318.
34. For reviews, see: Molander, G. A. Org. React. 1994, 46, 211-367. Molander, G. A. Chem. Rev. 1992, 92, 29-68. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. For a similar reduction problem and an alternative solution, see: Wang, T.-Z.; Pinard, E.; Paquette, L. A. J. Am. Chem. Soc. 1996, 778, 1309-1318.
35. For reviews, see: Molander, G. A. Org. React. 1994, 46, 211-367. Molander, G. A. Chem. Rev. 1992, 92, 29-68. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. For a similar reduction problem and an alternative solution, see: Wang, T.-Z.; Pinard, E.; Paquette, L. A. J. Am. Chem. Soc. 1996, 778, 1309-1318.
36. For reviews, see: Molander, G. A. Org. React. 1994, 46, 211-367. Molander, G. A. Chem. Rev. 1992, 92, 29-68. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. For a similar reduction problem and an alternative solution, see: Wang, T.-Z.; Pinard, E.; Paquette, L. A. J. Am. Chem. Soc. 1996, 778, 1309-1318.
37. max range 2.54-26.01°, 3641 measured reflections, 3369 [R(int) = 0.0277] independent reflections, R(1) [ I > 2σ(I)] = 0.0468, wR2 [all data] = 0.1063, GOF (all data) = 0.970 (1.147).
38. For a related example, see: White, J. D.; Cutshall, N. S.; Kim, T.-S.; Shin, H. J. Am. Chem. Soc. 1995, 117, 9780-9781.
39. Molecular modeling was performed on a Silicon Graphics MD25G workstation running Insight II Discover, version 2.3.0 (Biosym Technologies, San Diego). The structure was energy minimized with the force field cvff.frc. and the minimization algorithm VA09A. The diastereomer 9 was found to be 1.1 kcal/mol lower in energy than 6.
40. max range 3.97-67.48°, 2983 measured reflections, 2842 [R(int) = 0.0395] independent reflections, R(1) [I > 2σ(I)] = 0.0467, wR2 [all data] = 0.1425, GOF (all data) = 1.101 (1.134).
41. 3d this work also constitutes, in a formal sense, the synthesis of natural 9-acetoxyfukinanolide.
42. Dictionary of Terpenoids; Connolly, J. D., Hill, R. A., Eds.; Chapman and Hall: New York, 1991; Vol. 1, p 566 and references cited therein.