Defensive mechanisms of arthropods .144. Absolute configuration of insect-produced epilachnene

[摘要] Samples of (R) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide] were synthesized from (R) and(S)-norvaline. The diastereomeric alpha-methoxy-alpha-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) alpha-methoxy-alpha-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. (C) 1997 Elsevier Science Ltd.

[发布日期] 1997-04-21