Short Synthesis of the Antidiabetic Octaketide Ethyl 2-(2,3,4-Trimethoxy-6-octanoylphenyl)acetate

Abstract

A facile and practical approach for the synthesis of ethyl 2-(2,3,4-trimethoxy-6-octanoylphenyl)acetate, an antidiabetic octaketide analogue of cytosporone B, is described. Unlike known approaches for the synthesis of cytosporones and their analogues, the key step of the developed route is a Friedel–Crafts alkylation of 1-(3,4,5-trimethoxyphenyl)octan-1-one with ethyl chloro(methylthio)acetate, followed by desulfurization.

Key words

cytosporones - octaketides - TMPA - Friedel–Crafts reaction - alkylation - medicinal chemistry

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