Application of the 2-azaallyl anion cycloaddition method to an enantioselective total synthesis of (+)-coccinine

Angewandte Chemie - International Edition

Volumn 37, Issue 12, 1998, Pages 1724-1726

  Pearson, William H ^a   Lian, Brian W ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Alkaloids; Cycloadditions; Nitrogen heterocycles; Synthetic methods; Total synthesis

Indexed keywords

EID: 0032479255     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980703)37:12<1724::AID-ANIE1724>3.0.CO;2-8     Document Type: Article

References (33)

1. S. F. Martin in The Alkaloids, Vol. 30 (Ed.: A. Brossi), Academic Press, New York, 1987, pp. 251-376.
2. F. Viladomat, J. Bastida, C. Codina, W. E. Campbell, S. Mathee, Phytochemistry 1995, 40, 307-311.
3. a) L. E. Overman, J. Shim, J. Org. Chem. 1991, 56, 5005-5007;
4. b) ibid. 1993, 58, 4662-4672.
5. a) M. Ishizaki, O. Hoshino, Y. Iitaka, Tetrahedron Lett. 1991, 32, 7079-7082;
6. b) M. Ishizaki, O. Hoshino, Y. Iitaka, J. Org. Chem. 1992, 57, 7285-7295;
7. c) M. Ishizaki, K. Kurihara, E. Tanazawa, O. Hoshino, J. Chem. Soc. Perkin Trans. 1 1993, 101-110.
8. a) J. Jin, S. M. Weinreb, J. Am. Chem. Soc. 1997, 119, 2050-2051;
9. b) J. Jin, S. M. Weinreb, J. Am. Chem. Soc. 1997, 119, 5773-5784.
10. a) W. H. Pearson, D. P. Szura, W. G. Harter, Tetrahedron Lett. 1988, 29, 761-764;
11. b) W. H. Pearson, D. P. Szura, M. J. Postich, J. Am. Chem. Soc. 1992, 114, 1329-1345;
12. c) W. H. Pearson, M. J. Postich, J. Org. Chem. 1992, 57, 6354-6357.
13. For a review of early work in this area, see T. Kauffmann, Angew. Chem. 1974, 86, 715-727; Angew. Chem. Int. Ed. Engl. 1974, 13, 627-639.
14. For a review of early work in this area, see T. Kauffmann, Angew. Chem. 1974, 86, 715-727; Angew. Chem. Int. Ed. Engl. 1974, 13, 627-639.
15. For related reactions of α-metalated vinyl sulfides with epoxides, see a) K. Oshima, K. Shimoji, H. Takahishi, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1973, 95, 2694-2695; b) I. Vlattas, L. D. Veccia, A. O. Lee, J. Am. Chem. Soc. 1976, 98, 2008-2010.
16. For related reactions of α-metalated vinyl sulfides with epoxides, see a) K. Oshima, K. Shimoji, H. Takahishi, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1973, 95, 2694-2695; b) I. Vlattas, L. D. Veccia, A. O. Lee, J. Am. Chem. Soc. 1976, 98, 2008-2010.
17. a) W. H. Pearson, M. J. Postich, J. Org. Chem. 1994, 59, 5662-5671;
18. b) W. H. Pearson, F. E. Lovering, Tetrahedron Lett. 1994, 35, 9173-9176;
19. c) W. H. Pearson, F. E. Lovering, J. Am. Chem. Soc. 1995, 117, 12336-12337.
20. M. J. Postich, PhD thesis, University of Michigan (USA), 1994.
21. E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972, 3769.
22. P. A. Magriotis, J. T. Brown, M. E. Scott, Tetrahedron Lett. 1991, 32, 5047-5050.
23. While the tin-lithium exchange and protonation sequence proceeds via the vinyllithium compound required for the epoxide-opening step in Scheme 2, it is best generated by deprotonation of purified 17.
24. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, X.-L. Zhang, J. Org. Chem. 1992, 57, 2768-2771.
25. a) N. Adje, P. Breuilles, D. Uguen, Tetrahedron Lett. 1993, 34, 4631-4634; the method of Takano et al. was used:
26. b) S. Takano, M. Akiyama, S. Sato, K. Ogasawara, Chem. Lett. 1983, 1593-1596.
27. Meyers method, as modified by Overman et al., was used: a) F. W. Collington, A. I. Meyers, J. Org. Chem. 1971, 36, 3044-3045; b) S. D. Knight, L. E. Overman, G. Pairaudeau, J. Am. Chem. Soc. 1995, 117, 5776-5788.
28. Meyers method, as modified by Overman et al., was used: a) F. W. Collington, A. I. Meyers, J. Org. Chem. 1971, 36, 3044-3045; b) S. D. Knight, L. E. Overman, G. Pairaudeau, J. Am. Chem. Soc. 1995, 117, 5776-5788.
29. For the asymmetric dihydroxylation of allylic bromides in with 72% ee or lower, see H. C. Kolb, Y. L. Bennani, K. B. Sharpless, Tetrahedron: Asymmetry 1993, 4, 133-141.
30. M. J. Eis, J. E. Wrobel, B. Ganem, J. Am. Chem. Soc. 1984, 106, 3693-3694.
31. The success of the epoxide opening was very sensitive to the reaction conditions and the nature of the protecting groups. A discussion will appear in the full account of this work.
32. We thank Dr. Henry Fales of the National Institutes of Health for samples of (-)-montanine and (-)-coccinine, and Professor Osamu Hoshino of the Science University of Tokyo for spectra of montanine.
33. [6b, 9] The alternate chairlike conformation that may lead to 33 is not shown, since it displays severe 1,3-diaxiallike interactions.