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

Article abstract of DOI:10.1246/bcsj.64.1471

(+)-Grandisol, an insect pheromone having cyclobutane skeleton, is synthesized enantio- and diastereoselectively.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.