Synthesis of rebeccamycin and 11-dechlororebeccamycin

Authors
Faul, MM Winneroski, LL Krumrich, CA
Citation
Mm. Faul et al., Synthesis of rebeccamycin and 11-dechlororebeccamycin, J ORG CHEM, 64(7), 1999, pp. 2465-2470
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
7
Year of publication
1999
Pages
2465 - 2470
Database
ISI
SICI code
0022-3263(19990402)64:7<2465:SORA1>2.0.ZU;2-8
Abstract
Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% y ield from 7-chloroindole (1), was condensed with methyl 7-chloroindole-3-gl yoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimid es 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followe d by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11-dechlororebeccamycin.