BROAD-SPECTRUM SYNTHESIS OF ENANTIOMERICALLY PURE LACTONES .1. SYNTHESIS OF SEX-PHEROMONES OF THE CARPENTER BEE, ROVE BEETLE, JAPANESE BEETLE, BLACK-TAILED DEER, AND ORIENTAL HORNET

Enantiomerically pure lactonic pheromones, 1, 3-6, of the carpenter bee, black-tailed deer, Japanese beetle, rove beetle, and Oriental hornet, respectively, have been synthesized from racemic type 7 cyano alcohols. The key to the success of the overall approach is the facile separation of diastereomeric carbamates derived from type 7 cyano alcohols by automated multigram LC. The approach chosen also facilitates the assignment of absolute configurations to the lactone enantiomers and their precursors. In the case of 1 and 2, direct determination of enantiomeric purity and absolute configuration is also possible using the chiral solvating agent 2, 2, 2-trifluoro-l-(9-anthryl)ethanol. © 1979, American Chemical Society. All rights reserved.