C-10-10 DETERMINING THE ABSOLUTE CONFIGURATION OF INSECT-PRODUCEDEPILACHNENE.

J.J. Farmer, A.B. Attygalle, S.R. Smedley, T. Eisner and J. Meinwold.
Baker Laboratory, Department of Chemistry, Cornell University, Ithaca, NY 14853, USA.

The absolute configuration of epilachnene (1)-a defensive alkaloid fromthe pupa of the coccinellid beetle Epilachna varivestis, was determinedby synthesis. Samples of (R)- and (S)-epilachnene were synthesizedfrom (R)- and (S)-norvaline. Gas chromatographic comparison of thediastereomeric Mosher amides of these synthetic samples with that of theinsect-produced epilachnene established the configuration of the naturalproduct.