Journal
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
Volume 70, Issue 1, Pages 72-84Publisher
INST ORGANIC CHEM AND BIOCHEM
DOI: 10.1135/cccc20050072
Keywords
indoles; Jacobson reaction; phytoalexins; benzocamalexin; glycosides; glycosidations; benzothiazoles; thioamides; nucleosides
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A linear synthesis of substituted 1-(beta-D-glucopyranosyl)benzocamalexins starting from indoline and penta-O-acetyl-beta-D-glucopyranose was elaborated. Jacobson cyclization of corresponding 4-substituted peracetylated beta-D-glucopyranosylindole-3-carbothioanilides employing potassium ferricyanide under basic conditions was a key synthetic step.
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