Transformation of Esters into 2‐Substituted Allyl Halides via Tertiary Cyclopropanols: Application in the Stereoselective Synthesis of (2<i>S</i>,3<i>S</i>,7<i>S</i>)‐3,7‐Dimethyl‐2‐pentadecyl Acetate, the Sex Pheromone of the Pine Sawfly <i>Neodiprion sertifer</i>

Abstract

Abstract (2 S ,3 S ,7 S )‐3,7‐Dimethyl‐2‐pentadecyl acetate ( ac‐1 ), the sex pheromone of the pine sawfly Neodiprion sertifer , has been newly synthesized by the transformation of the corresponding esters 8 and 12 into 2‐oxyalkyl‐substituted allyl bromides 4 and 5 via tertiary cyclopropanols 6 and 7 . (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2006)