Structure revision and syntheses of epohelmins A and B

Organic Letters

Volumn 7, Issue 20, 2005, Pages 4419-4422

  Snider, Barry B ^a   Gao, Xiaolei ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOHELMIN A; EPOHELMIN B; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 26444473551     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0516061     Document Type: Article

References (28)

1. (a) Sakano, Y.; Shibuya, M.; Yamaguchi, Y.; Masuma, R.; Tomada, H.; Ômura, S.; Ebizuka, Y. J. Antibiot. 2004, 57, 564-568.
2. (b) Ômura, S.; Kyoda, H.; Masuma, R.; Ebizuka, Y.; Shibuya, M. Japan Kokai Tokkyo Koho JP 2004196680, 2004;
3. Chem. Abstr. 2004, 141, 122412m.
4. Glass, R. S.; Deardorff, D. R.; Gains, L. H. Tetrahedron Lett. 1978, 2965-2968.
5. Subramanian, T.; Lin, C.-C.; Lin, C.-C. Tetrahedron Lett. 2001, 42, 4079-4082.
6. Poon, T. H. W.; Pringle, K.; Foote, C. S. J. Am. Chem. Soc. 1995, 177, 7611-7618.
7. Christine, C.; Ikhiri, K.; Ahond, A.; Mourabit, A. A.; Poupat, C.; Potier, P. Tetrahedron 2000, 56, 1837-1850.
8. (a) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107-4110.
9. (b) Okue, M.; Watanabe, H.; Kasahara, K.; Yoshida, M.; Horinouchi, S.; Kitahara, T. Biosci. Biotechnol. Biochem. 2002, 66, 1093-1096.
10. (a) Langley, D. R.; Thurston, D. E. J. Org. Chem. 1987, 52, 91-97.
11. (b) Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861-2863.
12. (c) Dolbeare, K.; Pontoriero, G. F.; Gupta, S. K.; Mishra, R. K.; Johnson, R. L. Bioorg. Med. Chem. 2003, 11, 4103-4112.
13. We thank Prof. M. Shibuya for a complete set of 1D and 2D NMR spectra of epohelmins A and B.
14. (a) Andrés, J. M.; Pedrosa, R.; Pérez, A.; Pérez-Encabo, A. Tetrahedron 2001, 57, 8521-8530.
15. (b) Hanson, G. J.; Baran, J. S.; Lindberg, T. Tetrahedron Lett. 1986, 27, 3577-3580.
16. For a similar compound see: Pommelet, J. C.; Jourdain, F.; Dhimane, H. Molecules 2000, 5, 1130-1138.
17. (a) Parker, K. A.; O'Fee, R. J. Am. Chem. Soc. 1983, 105, 654-655.
18. (b) Kiyooka, S.-i.; Nakano, M.; Shiota, F.; Fujiyama, R. J. Org. Chem. 1989, 54, 5409-5411.
19. (c) St-Denis, Y.; Chan, T.-H. J. Org. Chem. 1992, 57, 3078-3085.
20. Provot, O.; Célérier, J.-P.; Lhommet, G. J. Heterocycl. Chem. 1998, 35, 371-376.
21. For the assigned spectra of cis- and trans-3-methylpyrrolizidine, see: Skvortsov, I. M.; Antipova, I. V. J. Org. Chem. USSR 1979, 15, 777-783;
22. Zh. Org. Khim. 1979, 15, 868-875.
23. Chamberlin, A. R.; Chung, J. Y. L. J. Org. Chem. 1985, 50, 4425-4431.
24. Gundermann, H.; Schnekenburger, J. Arch. Pharm. (Weinheim) 1998, 321, 925-929.
25. (a) Corey, E. J.; Raju, N. Tetrahedron Lett. 1983, 24, 5571-5574.
26. (b) Oku, A.; Numata, M. J. Org. Chem. 2000, 65, 1899-1906.
27. (c) Mohapatra, S.; Capdevila, J. H.; Murphy, R. C.; Hevko, J. M.; Falck, J. R. Tetrahedron Lett. 2001, 42, 4109-4110.
28. Kwok, P.-Y.; Muellner, F. W.; Chen, C.-K.; Fried, J. J. Am. Chem. Soc. 1987, 109, 3684-3692.