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Synthesis of 18R-hydroxy-epiallo-yohimbines from (−)-3-iso-19,20-dehydro-β-yohimbine: an enantiospecific route to deserpidine and reserpine analogues from secologanin

✍ Scribed by Falmai Binns; Richard T Brown; Bukar E.N Dauda

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 126 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00913-8

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✦ Synopsis

^)-3-Iso-19,20-dehydro-b-yohimbine has been converted into epiallo-yohimbines and, via a novel regioand stereoselective hydration, into the 18R-hydroxy derivative, an analogue of deserpidine. Its 11-methoxy derivative, also prepared from secologanin, is a potential precursor for a reserpine analogue.

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Enantiospecific synthesis of (−)-3-iso-19,20-dehydro-β-yohimbine from secologanin: a route to normal and pseudo stereoisomers of yohimbine

✍ Richard T Brown; Simon B Pratt; Paul Richards 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 129 KB

Hydrolysis of secologanin ethylene acetal at pH 7 resulted in stereoselective aldol cyclisation to a cyclohexene aldehyde, which, on reductive amination and cyclisation with tryptamine aorded (^)-3-iso-19,20dehydro-b-yohimbine, converted into various normal and pseudo isomers of yohimbine.