Abstract
The syntheses of sex pheromones (trans-11-tetradecen-1-ol [12], trans-7-dodecenyl acetate [13], trans-9-dodecenyl acetate [14], trans-11-tetradecenyl acetate [15], and trans-11-tetradecenal [16]) secreted by Lepidoptera of female insects have been examined systematically by the standard methods using general reagents (Fig.-1).
Dehydrogenation of 1, 7-heptanediol [1], 1, 9-nonanediol [2], 1, 11-undecanediol [3] led to 7-hydroxyheptanal [4], 9-hydroxynonanal [5], 11-hydroxyundecanal [6] respectively (Table-2). 12-Hydroxy-trans-5-dodecen-4-one [7] was derived from [4] by the condensation with methyl propyl ketone in the presence of the base, and also 12-hydroxy-trans-5-dodecen-2-one [8] and 14-Hydroxy-trans-5-tetradecen-2-one [9] derived from [5] and [6] with acetone respectively. trans-7-dodecen-1-ol [10], trans-9-dodecen-1-ol [11] and [12] were prepared by Wolff-Kishner reduction of [7][9], and [13][15] followed by esterification of [10][12]. And also, [16] was easily derived from [15] by dehydrogenation. Thus sex pheromones [12][16] were synthesized by the standard method.
