Enantio- and Diastereo-Selective Synthesis of (+)-Grandisol

Abstract

(+)-Grandisol, an insect pheromone having cyclobutane skeleton, is synthesized enantio- and diastereo-selectively. The key steps in the synthesis are the asymmetric [2+2] cycloaddition reaction catalyzed by a chiral titanium reagent and the diastereoselective conjugate addition reaction by the combined use of Me2CuLi and trimethylsilyl trifluoromethanesulfonate.