Regiospecific functionalization of dimetalated isopropenylacetylene, a synthetic equivalent of the isoprene" anion". An efficient synthesis of the bark beetle …

PAA Klusener, W Kulik, L Brandsma

Index: Klusener, Peter A. A.; Kulik, Willem; Brandsma, Lambert Journal of Organic Chemistry, 1987 , vol. 52, # 23 p. 5261 - 5266

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Citation Number: 29

Abstract

Regiospecific (mono) functionalization of dilithiated isopropenylacetylene LiCWC (= CH2) CH2Li with a large number of electrophilic reagents (“E+”) gave the compounds HC= CC (= CH2) CH2E in high yields. Coupling with (CH3) 2CHCH2CH= 0 and (CHd2C= CHCH= 0, followed by partial reduction of the triple bond with activated zinc powder, gave the bark beetle pheromones ipsenol and ipsdienol, respectively, in> 55% overall yields.