ChemInform Abstract: Ring Expansion of Cyclopropylmethanols to Cyclobutanes - An Enantioselective Total Synthesis of (R)-(+)-Dodecan-5-olide, and (S)-(+ )- and (R)-(-)-5-((Z)-Dec-1-enyl)dihydrofuran-2(3H)-one.

Abstract

A novel and convenient route to chiral cyclobutanones (8) and (9) by ring expansion of the Cyclopropylmethanols (6) and (7) was developed, leading to an enantioselective total synthesis of (R)–(+)-dodecan-5-olide (25), and (S)-(+)- and (R)–(-)-5-[(Z)-dec-1-enyl]dihydrofuran-2(3H)-one (35) and (36)(the pheromone of the Japanese beetle).