A versatile approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid

Article abstract of DOI:10.1007/BF02495617

A general approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid was developed. The method comprises the conversion of the acid into undec-10-enyl acetate, shortening of its carbon chain to afford dec-9-enyl acetate (via 11-acetoxyundecanoic acid), and a two-step transformation of the latter into the key intermediate, dec-9-yn-1-ol, by sequential bromination - dehydrobromination. The elimination of two HBr molecules from the dibromide is effectively performed using Bu¹OK in the presence of dibenzo-18-crown-6 as the catalyst.