Transformation of Esters into Allyl Halides via Substituted Cyclopropanols. Application in the Synthesis of (2S,3R,7R/S)‐3,7‐Dimethyltridec‐2‐yl Acetate and Propionate, Sex Attractants of Pine Sawfly Diprion pini.

Abstract

Abstract A convenient new approach to the synthesis of the acetate and the propionate of (2 S ,3 R ,7 R / S )-3,7-dimethyltridecan-2-ol, sex attractants of Diprion pini L., using the cyclopropanation of the ethoxycarbonyl group in O -THP protected ethyl ( S )-lactate with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide followed by C-2–C-3 cyclopropane ring opening as the key steps has been performed.