The first total synthesis of (±)-Saudin [11]

Journal of the American Chemical Society

Volumn 121, Issue 32, 1999, Pages 7425-7426

  Winkler, Jeffrey D ^a   Doherty, Elizabeth M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PLANT EXTRACT; SAUDIN; UNCLASSIFIED DRUG;

DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; NONHUMAN; PLANT LEAF; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033581168     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9916198     Document Type: Letter

References (20)

1. Mossa, J. S.; Cassady, J. M.; Antoun, M. D.; Byrn, S. R.; McKenzie, A. T.; Kozlowski, J. F.; Main, P. J. Org. Chem. 1985, 50, 916-918.
2. Mossa, J. S.; El-Denshary, E.; Hindawi, R.; Ageel, A. Int. J. Crude Drug Res. 1988, 26, 81-87.
3. (a) Boeckman, R. K.; Neeb, M. J.; Gaul, M. D. Tetrahedron Lett. 1995, 36, 803-806.
4. (b) Labadie, G. R.; Cravero, R. M.; Gonzalez-Sierra, M. Synth. Commun. 1996, 26, 4671-4684.
5. Winkler, J.; Mazur, C.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020.
6. Winkler, J. D.; Doherty, E. M. Tetrahedron Lett. 1998, 2253-2256.
7. Oppolzer, W.; Battig, K.; Hudlicky, T. Tetrahedron 1981, 37, 4359-4364.
8. Reid, E. B.; Fortenbaugh, R. B.; Patterson, H. R. J. Org. Chem. 1950, 15, 2-582.
9. White, J. D.; Takabe, K.; Prisbylla, M. P. J. Org. Chem. 1985, 50, 5233-5244.
10. Fang, Y. Ph.D. Dissertation, University of Rochester, 1991.
11. Miller, R. D.; McKean, D. R. Synthesis 1979, 730-732.
12. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
13. For other examples of this reduction side product see: (a) Garland, R. B.; Miyano, M.; Pireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854-5861. (b) Lord, M. D.; Negri, J. T.; Paquette, L. A. J. Org. Chem. 1995, 60, 191-195.
14. For other examples of this reduction side product see: (a) Garland, R. B.; Miyano, M.; Pireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854-5861. (b) Lord, M. D.; Negri, J. T.; Paquette, L. A. J. Org. Chem. 1995, 60, 191-195.
15. (a) Hirota, K.; Isobe, Y.; Maki, Y. J. Chem. Soc., Perkin Trans. 1 1989, 2513-2514.
16. (b) Saulnier, M. G.; Kadow, J. F.; Tun, M. M.; Langley, D. R.; Vyas, D. M. J. Am. Chem. Soc. 1989, 111, 8320-8321.
17. Barnick, J. W. F. K.; Van der Baan, J. L.; Bickelhaupt, F. Synthesis 1979, 787-788.
18. Sato, M.; Ogasawara, H.; Oi, K.; Kato, T. Chem. Pharm. Bull. 1983, 31, 1896.
19. Jager, G. Chem. Ber. 1972, 105, 137-149.
20. Winkler, J.; Shao, B. Tetrahedron Lett. 1993, 3355-3358.