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- Title
Total Synthesis of Indole and Dihydroindole Alkaloids. IX Studies on the synthesis of bisindole alkaloids in the vinblastine- vincristine series. The biogenetic approach.
- Authors
Kutney, James P.; Hibino, Toshihiko; Jahngen, Edwin; Okutani, Tetsuya; Ratcliffe, Arnold H.; Treasurywala, Adi M.; Wunderly, Stephen
- Abstract
A detailed study of the reaction of catharanthine N-oxide and vindoline has been carried out employing various conditions. Under optimum conditions, which involve low temperatures and trifluoroacetic anhydride as reagent, 3′, 4′-dehydrovinblastine (XIII, R = COOCH3), in reasonable yields is essentially the exclusive product. However two additional products, 18′ ( epi)- 3′, 4′-dehydrovinblastine (XIV, R = COOCH3) and 1′-hydroxy- 3′, 4′-dehydrovinblastine (XVI, R = COOCH3) are also often isolated. The reaction, which follows the course of a Polonovski-type fragmentation process, has been extended to the N-oxide derivatives of dihydrocatharanthine and decarbomethoxycatharanthine to provide again a series of bisindole alkaloid derivatives, also vinblastines. A mechanistic rationale is provided to explain the various results obtained.
- Publication
Helvetica Chimica Acta, 1976, Vol 59, Issue 8, p2858
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19760590824