Synthesis of 18-hydroxyvincamines and epoxy-1,14-seco-vincamines; A new proof for the aspidospermane-eburnane rearrangement

Chemical transformations started from tabersonine were studied. A one-pot oxidative ring-transformation with permaleic acid in methanol yielded 17,18-dehydrovincamine. Hydroboration-oxidation of the latter compound led to alkaloid 17,18-dehydrovincamone. Hydroboration-oxidation of tabersonine result...

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Bibliographic Details
Published inHeterocycles Vol. 71; no. 11; pp. 2347 - 2362
Main Authors Nemes, Andras, Szantay, Csaba, Czibula, Laszlo, Greiner, Istvan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
VINCA ALKALOIDS
TABERSONINE
METHYLENE-INDOLINES
VINCADIFFORMINE
INDOLENINES
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Summary:Chemical transformations started from tabersonine were studied. A one-pot oxidative ring-transformation with permaleic acid in methanol yielded 17,18-dehydrovincamine. Hydroboration-oxidation of the latter compound led to alkaloid 17,18-dehydrovincamone. Hydroboration-oxidation of tabersonine resulted 14 beta-hydroxyvineadifformine and 15p-hydroxyvincadifforinine. Allowing 14 beta- and 15 beta- hydroxyvincadifformines to react with permaleic acid/methanol provided 1,14-secovincamines, serving as new evidence for the mechanism of the aspidospermane-eburnane transformation. On the other hand 18 beta-hydroxyvincamine was obtained from 14 beta-hydroxyvincadifformine by reaction with 3-chloroperbenzoic acid and successive treatment with triphenylphosphine/aqueous acetic acid.
ISSN:0385-5414
DOI:10.3987/COM-07-11114