Asymmetric route to the hydroindolone core of the Amaryllidaceae alkaloids employing chiral bicyclic lactams

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1519-1522

  Watson, Daniel J ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; ALKALOID DERIVATIVE; HAEMANTHIDINE; INDOLE DERIVATIVE; LACTAM DERIVATIVE; PRETAZETTINE; TAZETTINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DRUG STRUCTURE; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034603347     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02328-X     Document Type: Article

References (23)

1. Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, p. 251.
2. Furusawa, E.; Irie, H.; Combs, D.; Wildman, W. C. Chemotherapy (Basel) 1980, 26, 36 and references cited therein.
3. (a) Furusawa, E.; Furusawa, S.; Lee, J. Y. B.; Patanavanich, S. Proc. Soc. Expl. Biol. Med. 1976, 152, 186 and references cited therein.
4. (b) Furusawa, E.; Furusawa, S.; Lee, J. Y. B.; Patanavanich, S. Chemotherapy (Basel) 1983, 29, 294 and references cited therein.
5. © Furusawa, E.; Furusawa, S. Onocology 1988, 45, 180.
6. Hendrickson, J. B.; Bogard, T. L.; Fisch, M. E.; Grossert, S.; Yoshimura, N. J. Am. Chem. Soc. 1974, 96, 7781.
7. Tsuda, Y.; Ukai, A.; Isobe, K. Tetrahedron Lett. 1972, 3153.
8. Danishefsky, S.; Morris, J.; Mullen, G.; Gammill, R. J. Am. Chem. Soc. 1982, 106, 7591.
9. White, J. D.; Chong, W. K. M.; Thirring, K. J. Org. Chem. 1983, 48, 2300.
10. (a) Martin, S. F.; Davidsen, S. K.; Puckette, T. A. J. Org. Chem. 1987, 52, 1962.
11. (b) Martin, S. F.; Davidsen, S. K. J. Am. Chem. Soc. 1984, 106, 6431.
12. Abelman, M. M.; Overman, L. E.; Tran, V. D. J. Am. Chem. Soc. 1990, 112, 6959.
13. Rigby, J. H.; Cavezza, A.; Heeg, M. J. J. Am. Chem. Soc. 1998, 120, 3664.
14. (a) Overman, L. E.; Wild, H. Tetrahedron Lett. 1989, 30, 647.
15. (b) Ishibashi, H.; Nakatani, H.; Iwami, S.; Sato, T.; Nakamura, N.; Ikeda, M. J. Chem. Soc., Chem. Commun. 1989, 1767.
16. Nishimata, T.; Mori, M. J. Org. Chem. 1998, 63, 7586.
17. Meyers, A. I.; Hanreich, R.; Wanner, K. T. J. Am. Chem. Soc. 1985, 107, 7776.
18. Stowell, J. C.; King, B. T.; Hauck Jr., H. F. J. Org. Chem. 1983, 48, 5381.
19. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
20. Ireland, R. E.; Varney, M. D. J. Org. Chem. 1986, 51, 635.
21. Branalt, J.; Kvarnstrom, I.; Svensson, S. C. T. J. Org. Chem. 1994, 59, 4430.
22. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897.
23. Meyers, A. I.; Lefker, B. A.; Wanner, K. T.; Aitken, R. A. J. Org. Chem. 1986, 51, 1936.