INSECT PHEROMONES AND THEIR ANALOGUES. IX. STEREOSPECIFIC SYNTHESIS OF (Z)-DODECA-9,11-DIENYL ACETATE, A COMPONENT OF THE SEX PHEROMONE OF THE COTTON BOLLWORM MOTH Diparopsis cactanea

Article abstract of DOI:10.1007/BF00575767

A method has been developed for the stereospecific synthesis of (Z)-dodeca-9,11-dienyl acetate, a component, together with the corresponding (E) isomer, of the sex pheromone of the red cotton bollworm moth, that is based on the coupling of vinylacetylene with either 8-hydroxyoctanal or 8-bromoctan-1-ol to form a C₁₂ enynic compound in which the acetylenic bond is then reduced stereospecifically with 9-borabicyclo<3.3.1>nonane.