Synthesis of optically active 2-furylmethanols as useful chiral building blocks and its application to the synthesis of (5R,6S)-6-acetoxyhexadecan-5-olide and (+)-disparlure

Abstract

Kinetic resolution of racemic secondary 2-furylmethanols using catalytic amounts of the titanium(IV)–tartrate complex was achieved successfully, providing optically active 2-furylmethanols (80–>98% ee) and corresponding pyranones. (S)-1-(2-Furyl)undecanol (1f) was utilised as a chiral building block in the synthesis of (5R,6S)-6-acetoxyhexadecan-5-olide and (+)-disparlure.