Total synthesis of (-)-stemonine

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3361-3364

  Williams, David R ^a   Shamim, Khalida ^a   Reddy, Jayachandra P ^a   Amato, George S ^a   Shaw, Stephen M ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BUTYROLACTONE; IODINE; PYRROLIDINE DERIVATIVE; STEMONINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; WITTIG REACTION;

ALKALOIDS; AZEPINES; CYCLIZATION; IODINE; LACTONES; MOLECULAR STRUCTURE; PYRROLIDINES; STEMONACEAE; STEREOISOMERISM;

EID: 0141632651     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035368q     Document Type: Article

References (33)

1. Dahlgren, R. M. T.; Clifford, H. T.; Yeo, P. F. The Families of the Monocotyledons. Structure Evolution and Taxonomy; Springer-Verlag: Berlin, 1985.
2. (a) Sakata, K.; Aoki, K.; Chang, C.-F., Sakurai, A.; Tamura, S.; Murakoshi, S. Agric. Biol. Chem. 1978, 42, 457. (b) Shinozaki, H.; Ishida, M. Brain. Res. 1985, 334, 33. (c) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1205.
3. (b) Shinozaki, H.; Ishida, M. Brain. Res. 1985, 334, 33.
4. (c) Ye, Y.; Qin, G.-W.; Xu, R.-S. Phytochemistry 1994, 37, 1205.
5. For recent reviews, see: (a) Pilli, R. A.; Ferriera de Oliviera, M. Nat. Prod. Rep. 2000, 17, 117. (b) Ye, Y.; Qin, G.-W.; Xu, R.-S. J. Nat. Prod. 1994, 57, 665.
6. For recent reviews, see: (a) Pilli, R. A.; Ferriera de Oliviera, M. Nat. Prod. Rep. 2000, 17, 117. (b) Ye, Y.; Qin, G.-W.; Xu, R.-S. J. Nat. Prod. 1994, 57, 665.
7. Suzuki, K. J. Pharm. Soc. Jpn. 1929, 49, 457.
8. Suzuki, K. J. Pharm. Soc. Jpn. 1931, 51, 419
9. Koyama, H.; Oda, K. J. Chem. Soc. B. 1970, 1330.
10. Williams, D. R.; Brown, D. L.; Benbow, J. M. J. Am. Chem. Soc. 1989, 111, 1923
11. (a) Williams, D. R.; Fromhold, M. G.; Earley, J. D. Org. Lett. 2001, 3, 2721.
12. (b) Padwa, A.; Gin, J. D. Org. Lett. 2002, 4, 1515.
13. (c) Kende, A. S.; Hernando, J. I. M.; Milbank, J. B. J. Tetrahedron 2002, 58, 61.
14. (d) Wipf, P.; Rector, S. R.; Takahashi, H. J. Am. Chem. Soc. 2002, 124, 14848
15. (e) Kende, A. S.; Smalley, T. L.; Huang, H. J. Am. Chem. Soc. 1999, 121, 7431 and refs cited therein.
16. White, J. D.; Reddy, N. G.; Spessard, G. O. J. Am. Chem. Soc. 1988, 110, 1624.
17. (a) Pattenden, G.; Wiedenau, P. Tetrahedron Lett. 1997, 38, 3647.
18. (b) Boutellier, M.; Wallach, D.; Tamm, C. Helv. Chim. Acta 1993, 76, 2515.
19. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
20. (b) Negishi, E.-I.; Swanson, D. R.; Rousser, C. J. J. Org. Chem. 1990, 55, 5406.
21. Lactone 3 has been previously described via the asymmetric aldol condensation of imide i to give ii followed by silyl ether cleavage. Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417.
22. (a) Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
23. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099.
24. Optimal results were obtained with freshly opened bottles of 15-crown-5 (Aldrich), which may provide traces of water. However, older bottles of 15-crown-5 led to reduced yields of 15. Small amounts (4-8%) of the tetrahydrofuran i were also obtained as a minor product.
25. (a) Guidon, Y.; Morton, H. E.; Yoakim, C. Tetrahedron Lett. 1983, 24, 3969.
26. (b) Guidon, Y.; Morton, H. E.; Yoakim, C. J. Org. Chem. 1984, 49, 3912.
27. Schreiber, S. L.; Ikemoto, N. J. Am. Chem. Soc. 1992, 114, 2535.
28. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
29. Imine could be isolated following rapid purification via flash silica gel chromatography but decomposed within 2 h at room temperature. Spectral data for characterization of the imine are included in Supporting Information.
30. (a) Williams, D. R.; Osterhout, M. H.; McGill, J. M. Tetrahedron Lett. 1989, 30, 1327.
31. (b) Williams, D. R.; Osterhout, M. H.; McGill, J. M. Tetrahedron Lett. 1989, 30, 1331.
32. 3) with careful monitoring by TLC.
33. 1H NMR, IR, and mass spectra of the natural product.