Absolute configuration of insect-produced epilachnene

This is the authors' abstract. We don't add key points for this paper.

Samples of (R) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide] were synthesized from (R) and (S)-norvaline. The diastereomericα-methoxy-α-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) α-methoxy-α-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene.