Transformation of esters into allyl halides via substituted cyclopropanols. Application in the synthesis of (2 S,3 R,7 R/ S)-3,7-dimethyltridec-2-yl acetate and propionate, sex attractants of pine sawfly Diprion pini

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.