Douglas fir tussock moth Orgyia pseudotsugata

Grant, G. G., Tracey, A. S. and Hulme, M. (1997). (Z)-6,( >8-I Icneicosadicne-11 -one Synergistic sex pheromone component of Douglas-fir tussock moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera Lymantriidae)../. Chem. Ecol., 23, 19-34. 

Following is the stnictural formula of the principal sex pheromone of the Douglas fir tussock moth (Orgyia pseudotsugata), a severe defoliant of the fir trees of western North America. 

Another atypical Lepidopteran sex pheromone is the Z unsaturated ketone (580, Scheme 98) produced by the Douglas-fir tussock moth (Orgyia pseudotsugata). The acetylenic ketone (577), produced via a dithiane intermediate, was used by Smith et al. (255, 25(5) to prepare both the Z- and f-isomers (580 and 582, respectively) (Scheme 98). Kocienski and Cernigliaro (257) and Mori et al. (194) used an Eschen-moser cleavage of an alkyl substituted a,P-epoxy ketone to obtain straight chain acetylenic ketones that were transformed into (580) (Schemes 99 and 100, respectively). Acetylenic alcohol (578) has also been prepared by Grignard reactions (258, 259). 

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