STRUCTURE CONFIRMATION OF THE 4 TRANS-ISOMERS OF CERALURE, A MEDFLY ATTRACTANT, BY NMR

A series of one- and two-dimensional NMR experiments were used to conf irm structures of the four racemic trans isomers of ceralure, ethyl 4- (or 5)-iodo-trans-2-methylcyclohexane-1-carboxylate, a synthetic attra ctant for the male Mediterranean fruit fly, Ceratitis capitata (Wiedem ann). Proton and carbon assignments were made on the basis NMR data ob tained from 2D chemical shift correlation maps, attached proton tests, and 2D-H-1 homonuclear correlation spectroscopy. Assignments of confi guration and conformation, based on NMR, for the four trans isomers of ceralure (A, B-1, B-2, and C) were consistent with assignments previo usly derived from a comparison of the gas chromatographic elution beha vior of the trans isomers of ceralure and the traits isomer of trimedl ure, 1,1-dimethylethyl 4-(or 5)-chloro-trans-2-methylcyclohexane-1-car boxylate.