Abstract

An efficient enantiospecific total synthesis of ent-conduramine F-1 (aminocyclohexenetriol) was accomplished starting from the bis-Weinreb amide of tartaric acid. Key reactions in the synthesis include the desymmetrization of tartaric acid amide with vinylmagnesium bromide and installation of the required amine using Ellman sulfinimine. Ring closing metathesis was used to synthesize the required alkene in the cyclohexene.

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