58701-05-6Relevant academic research and scientific papers
SYNTHETIC INVESTIGATIONS IN THE FIELD OF INSECTS ATTRACTANTS (SEX ATTRACTANTS). XIV. STEREOSELECTIVE SYNTHESIS OF THE FOUR ISOMERS OF 6,11-HEXADECADIEN-1-OL AND THEIR ACETATES AND ALDEHYDES - COMPONENTS OF THE SEX PHEROMONES OF INSECTS OF THE FAMILY SATURNIIDAE (LEPIDOPTERA)
Rastegaeva, V. M.,Kovalev, B. G.,Kurts, A. L.,Bundel, Yu. G.
, p. 1866 - 1872 (2007/10/02)
The four isomers of 6,11-hexadecadien-1-ol, their acetates, and the corresponding aldehydes were obtained by a common scheme based on the alkylation of 5-hexyn-1-ol by the tetrahydropyranyl ether of 1,5-pentamethylene bromohydrin, stereoselective reduction of the triple bond in the alkylation product 11-(2-tetrahydropyranyloxy)-5-undecyn-1-ol, oxidation of the obtained Z or E isomer of 11-(2-tetrahydropyranyloxy)-5-undecen-1-ol to the aldehyde, and stereoselective olefination of the latter with pentylidenetriphenylphosphorane under the conditions of the formation of a doubl e bond with a specific (Z or E) configuration of the substituents.Subsequent removal of the tetrahydropyranyl protection of the alcohol group in the Wittig reaction products by acid hydrolysis gave 6,11-hexadecadien-1-ols, the acetylation or oxidation of which led to the corresponding acetates or aldehydes.The latter are components of the sex pheromones of insects of the Saturniidae family.
