Short Synthesis of the Antidiabetic Octaketide Ethyl 2-(2,3,4-Trimethoxy-6-octanoylphenyl)acetate
Synlett(2017)
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.
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Key words
cytosporones,octaketides,TMPA,Friedel-Crafts reaction,alkylation,medicinal chemistry
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