Synthesis of (±)-cis-tetradec-5-en-4-olide — The racemate of the sex pheromone of the Japanese beetle

Autor: Melikyan, G. G., Mkrtchyan, D. A., Lebedeva, K. V., Myaéorg, U. Yu., Panosyan, G. A., Badanyan, Sh. O.
Zdroj: Chemistry of Natural Compounds; January 1984, Vol. 20 Issue: 1 p94-98, 5p
Abstrakt: A three-stage method has been developed for the stereoselective synthesis of (±)-cis-tetradec-5-en-4-olide — the racemate of the sex pheromone of the Japanese beetlePopillia japonica C. The key reactions used were the stereoselective cis reduction of a triple bond with the aid of heterogeneous hydrogenation catalysts (zinc-copper couple, nickel boride, Lindlar catalyst) and the radical lactonization of conjugated systems by the action of acetic acid in the presence of manganese acetate.
Databáze: Supplemental Index