189251-21-6Relevant articles and documents
Absolute configuration of insect-produced epilachnene
Farmer, Jay J.,Attygalle, Athula B.,Smedley, Scott R.,Eisner, Thomas,Meinwald, Jerrold
, p. 2787 - 2790 (1997)
Samples of (X) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en olide] were synthesized from (R) and (S)-norvaline. The diastereomeric α-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.