Facile synthesis of (�)-2,6-dimethyloctan-1-ol formate, the biologically active analog of the smaller flour beetle aggregation pheromone, from 1-allyloxy- and 1-benzyloxy-2,6-dimethyl-2,7-octadienes, the telomers of isoprene with allyl and benzyl alcohols

Abstract

A careful investigation of the telomerization of isoprene with allyl, benzyl, 2-chloroethyl and methyl alcohols on π-allylpalladium complex catalysts was carried out. The structures of the obtained telomers were determined by1H NMR spectroscopy. 1-Alkoxy-2,6-dimethyl-2,7-octadiene is a predominant telomer. 2,6-Dimethyloctan-1-ol, which reacts with HCOOH to give (±)-2,6-dimethyloctan-1-ol formate in high yield, was obtained from 1-allyloxy- and 1-benzyloxy-2,6-dimethyl-2,7-octadienes by the removal of allyl and benzyl protective groups and by the hydrogenation of double bonds.