SYNTHESIS OF OPTICALLY PURE ENANTIOMERS OF GRANDISOL AND RELATED STUDIES.

摘要

Optically pure enantiomers of grandisol (cis-2-isopropenyl-1-methylcyclobutaneethanol), the putative aggregation pheromone of the white pine weevil, Pissodes strobi, were synthesized for testing in the field. The optical purity of the pheromone was established by resolving a key carboxylic acid. The completion of this synthesis depended on several useful studies: the Birch reduction of m-anisic acid, the use of NMR spectrometry to determine the optical purity of amine salts that are used to resolve carboxylic acids, a method of cleaving highly hindered -methylbenzyl amides, the ruthenium tetroxide catalyzed sodium periodate cleavage of allylic alcohols and, -unsaturated ketones, and the extreme sensitivity of grandisal (the corresponding aldehyde) to acids.