Absolute configuration of insect-produced epilachnene

Jay J. Farmer, Athula B. Attygalle, Scott R. Smedley, Thomas Eisner, Jerrold Meinwald

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)2787-2790
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number16
DOIs
StatePublished - 21 Apr 1997

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