Concise, asymmetric total synthesis of spirotryprostatin A

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3135-3137

  Onishi, Tomoyuki ^a   Sebahar, Paul R ^a   Williams, Robert M ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTIMITOTIC AGENT; AZOMETHINE YLIDE; OXINDOLE; SPIROTRYPROSTATIN A; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL CYCLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; PRENYLATION;

AZO COMPOUNDS; CYCLIZATION; INDOLE ALKALOIDS; PIPERAZINES; SPIRO COMPOUNDS; STEREOISOMERISM; TRYPTOPHAN;

EID: 0141743684     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0351910     Document Type: Article

References (26)

1. (a) Cui, C. B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 832.
2. (b) Cui, C. B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 51, 12651.
3. (c) Cui, C. B.; Kakeya, H.; Osada, H. Tetrahedron 1997, 53, 59.
4. Cui, C. B.; Kakeya, H.; Osada, H. Tetrahedron 1997, 53, 59.
5. (a) Cui, C. B.; Kakeya, H.; Okada, G.; Ubukata, M.; Takahashi, I.; Isono, K.; Osada, H. J. Antibiot. 1995, 48, 1382.
6. (b) Cui, C. B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. J. Antibiot. 1996, 49, 527.
7. (c) Cui, C. B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 534.
8. (a) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666.
9. (b) Sebahar, P. R.; Osada, H.; Usui, T., Williams, R. M. Tetrahedron 2002, 58, 6311.
10. (a) von Nussbaum, F.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39, 2175.
11. (b) Overman, L. E.; Rosen, M. D. Angew. Chem., Int. Ed. 2000, 39, 4596.
12. (c) Wang, H.; Ganesan, H. J. Org. Chem. 2000, 65, 4685.
13. (d) Bagul, T. D.; Lakshmaiah, G.; Kawabata, T.; Fuji, K. Org. Lett. 2002, 4, 249.
14. (e) Meyers, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 694.
15. For a review, see: (f) Lindel, T. Nach. Chem. 2000, 48, 1498.
16. (a) Edmonson, S. D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 1138.
17. (b) Edmonson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147.
18. Bell, S. E. V.; Brown, R. F. C.; Eastwood, F. W.; Horvath, J. M. Aust. J. Chem. 2000, 53, 183.
19. (a) Chan, T.-H.; Chang, E.; Vinokur, E. Tetrahedron Lett. 1970, 11, 1137.
20. (b) Hudrlik, P. F.; Peterson, D. Tetrahedron Lett. 1972, 13, 1785.
21. Giovannini, E.; Portmann, P. Helv. Chim. Acta 1948, 31, 1381.
22. NOEs were observed between the proton at position 4 of the oxindole and the proton at 8′a, between the proton at 6′ and the proton at 3′, and between the proton at 6′ and the proton at 4′.
23. Yamada, S.; Hongo, C.; Chibata, I. Agric. Biol. Chem. 1977, 41, 2413.
24. 2, these diastereomers could be isolated by PTLC.
25. A NOE was observed between the proton at position 4 of the oxindole and the olefinic proton of the 2-methyl-1-propenyl group. A NOE was also observed between the proton at position 4 of the oxindole and the proton at position 9.
26. Eguchi, C.; Kakuta, A. J. Am. Chem. Soc. 1974, 96, 3985.