An expedient route to the Calabar bean alkaloids (-)-physovenine and (-)-physostigmine

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2757-2759

  ElAzab, Adel S ^a   Taniguchi, Takahiko ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINESTERASE INHIBITOR; DRUG DERIVATIVE; PHYSOSTIGMINE; PHYSOVENINE;

ARTICLE; CHEMISTRY; LEGUME; MEDICINAL PLANT; STEREOISOMERISM; SYNTHESIS;

CHOLINESTERASE INHIBITORS; FABACEAE; PHYSOSTIGMINE; PLANTS, MEDICINAL; STEREOISOMERISM;

EID: 0034618292     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006065o     Document Type: Article

References (19)

1. Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Synthesis 1999, 341.
2. Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Chirality 2000, 12, 338.
3. Taniguchi, T.; Takeuchi, M.; Kadota, K.; ElAzab, A. S.; Ogasawara, K. Synthesis 1999, 1325.
4. Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 2609.
5. For reviews of the Calabar bean alkaloids, see: (a) Marion, L. The Alkaloids 1952, 2, 438.
6. (b) Coxworth, E. The Alkaloids 1967, 10. 383.
7. (c) Robinson, B. The Alkaloids 1971, 13, 213.
8. (d) Takano, S.; Ogasawara, K. The Alkaloids 1989, 36, 225.
9. For a most recent chiral synthesis, see: Matsuura, T.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6500.
10. For a previous chiral synthesis by the present group, see: Takano, S.; Moriya, M.; Ogasawara, K. J. Org. Chem. 1991, 56, 872.
11. For a most recent chiral synthesis, see: Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675.
12. For previous syntheses by the present group, see: (a) Takano, S.; Goto, E.; Hirama, M.; Ogasawara, K. Chem. Pharm. Bull. 1982, 30, 2641.
13. (b) Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. Heterocycles 1990, 31, 411.
14. (c) Takano, S.; Moriya, M.; Iwabuchi, Y.; Ogasawara, K. Chem. Lett. 1990, 109.
15. (d) Reference 7.
16. Welch, W. M. Synthesis 1977, 645.
17. Suginome, H.; Umeda, H.; Masamune, T. Tetrahedron Lett. 1970, 4571.
18. Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229.
19. Stahl, G. L.; Watter, R.; Smith, C. W. J. Org. Chem. 1978, 43, 2285.