Get access

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


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


original image

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).

Get access to the full text of this article