Application of the Chemo- and Enantioselective Cyclopropanation of Polyenes to the Total Synthesis of (+)-Bicyclohumulenone.

Abstract The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH 2 I) 2 was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield.