As. Pawar et S. Chattopadhyay, 10-UNDECENOIC ACID, AN INEXPENSIVE SOURCE FOR THE SYNTHESIS OF THE PHEROMONES OF COTTON PESTS, PEACH-TREE BORER AND CHERRY TREE BORER, Molecules, 2(6), 1997, pp. 87-90
The aldehyde 7, derived from 10-undecenoic acid (5) on cis-selective W
ittig reaction with pentylidenetriphenylphosphorane, subsequent deprot
ection and oxidation gave the pheromone (11Z)-hexadecenal (1). Wittig-
Horner olefination of 1 with the phosphonate 9 furnished the conjugate
d ester 10 which on base catalyzed isomerization to the (3Z)-ester 11
followed by LAH reduction and acetylation gave (3Z,13Z)-octadeadien-1-
yl acetate (2). Compound 10 on the other hand was chemoselectively red
uced and acetylated to furnish the pheromone (2E,13Z)-octadeadien-1-yl
acetate (4). For the synthesis of (3E,13Z)-octadeadien-1-yl acetate (
3), 1 was condensed with malonic acid under modified condition to affo
rd the acid 13 which was converted to 3 by standard reaction protocol.