Heterocycles

Synthesis of 18-hydroxyvincamines and epoxy-1, 14-secovincamines; a new proof for the aspidospermane-eburnane rearrangement

A Nemes, C Szántay Jr, L Czibula, I Greiner

Index: Nemes, Andras; Szantay Jr., Csaba; Czibula, Laszlo; Greiner, Istvan Heterocycles, 2007 , vol. 71, # 11 p. 2347 - 2362

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Citation Number: 10

Abstract

Abstract—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 14β- hydroxyvincadifformine and 15β-hydroxyvincadifformine. Allowing 14β-and 15β- ...