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Variable Synthesis of the Optically Active Thiotetronic Acid Antibiotics Thiolactomycin, Thiotetromycin, and 834-B1

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  • We are grateful to Prof. Dr. K. Ditrich (BASF AG, Ludwigshafen) for a donation of aldehyde 5.

Abstract

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In seven steps: The antibiotic (+)-thiolactomycin was synthesized in seven steps and with 16 % overall yield from 4-acetoxy-2-methyl-2-buten-1-al, an intermediate of the industrial synthesis of vitamin A. Key transformations were the catalytic asymmetric Sharpless epoxidation of an ethoxycarbonyl-substituted pentadienol (93 % ee) and a regio- and stereoselective thiolysis of the resulting epoxide (see scheme).

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