Synthesis of (±)-10-methyl-1-dodecanol acetate, the chiral component of the smaller tea tortrix moth (Adoxophyes sp.), with an option for asymmetric induction

Abstract

A new route to (±)-10-methyl-1-dodecanol acetate, a minor component of the smaller tea tortrix moth (Adoxophyes sp.), is described. An optional sequence that permits the generation of the chiral center with enantiomeric excesses (ee's) as high as 74% (R) or 80% (S) employing the available (S)-(−)-prolinol as a chiral auxiliary may be included. High-performance liquid chromatography of diastereomeric intermediates allows preparation of products with greater ee's.