New reaction of dicobalthexacarbonyl complexes of alkynes. Synthesis of (5Z)-tetradecenyl acetate – sex pheromone of scotia exclamationis
G. G. Melikian, V. M. Mkrtchian, K. A. Atanesian, G. Kh. Azarian, Sh. H. Badanian
Institute of Organic Chemistry, Academy of Sciences of the Armenian SSR, Yerevan
Abstract: A new way to the synthesis of (5Z)-tetradecenyl acetate, sex phoromono of A grotis (Scotia) Exclamationis L., has been elaborated. The key step is regioselective hydrogenolysis of C–C1 bond dicobalthexacarbonyl (DCHC) complex of methyl 4-chloro-5-tetradecynoate yielding methyl 5-tetradecynoate. In the absence of DCHC-group reduction with the zinc/acetic acid is accompanied with acetylene-allene isomerization, the main product being methyl 4,5-tetradecadienoate. The same approach is applied for the synthesis of some related bioactive compounds: (5Z)-decenyl-, (5Z)-undecenyl-, (5Z)-dodecenyl acetates.
Russian Journal of Bioorganic Chemistry 1990, 16 (7):1000-1001