The larval mandibular glands of the invasive insect Cactoblastis cactorum produce a complex mixture 2-acyl-4-acetoxy-cyclohexane-1,3-diones with the general structure 1  , where R is one of several unsaturated fatty acid derivatives. As part of a broader program to study the role these compounds play in larval chemical communication, we prepared the major components of the mixture by enantioselective synthesis. The key synthetic step was a Shi epoxidation of silylenol ether 2  to hydroxyketone 3,  which was elaborated to the desired compounds.

Enantioselective synthesis of 2-acyl-4-acetoxy-cyclohexane-1,3-diones

245th National Meeting (2013)

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