Douglas fir tussock moth sex pheromone

Smith, R.G., Daterman, G.E. andDaites, G.D. (1975). Douglas-fir tussock moth Sex pheromone identification and synthesis. Science, 188, 63-64. 

Hie anions of 68 and 79 are then useful acyl anion equivalents, but in natural product syntheses they are far less popular than reagents containing two sulphur atoms54, particularly dithians55. The chemistry of dithians, e. g. 86 and 87 has been well explored and they have been used in the synthesis of many natural products . The synthesis56 of the Douglas-Fir tussock moth sex pheromone 88 is an example of the way a dithian 86 acts as an acyl anion equivalent in ketone syntheses. 

The addition of an allylic group was reported in the synthesis of heneicos-6-en-ll-one, the sex pheromone of the Douglas fir tussock moth.67 This method was compared advantageously to the classical processes employing the toxic tin hydrides, with respect to the rates, yields, and chemoselectivity.68,69 Concerning the stereoselectivity however, no major difference exists between the conventional and sonochemical methods.70,71... 

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. 

The sex pheromone of the Douglas fir tussock moth, Previa pseudotsugata, constitutes the only ketonic sex pheromone that has been identified in a species of moth. This compound, (Z)-6-heneicosen-ll-one, is a powerful attractant for males both under laboratory and field conditions, as is the (E)-isomer (82). 

BrCl. Hydrolysis of lb to the acid and reaction with decyllithium results in 2, the sex pheromone of the Douglas fir tussock moth. 

Studies of the sex pheromone of the Douglas fir tussock moth required the synthesis of ( )-l,6-henicosadien-ll-one. Outline a synthesis of this ketone using (Q-5,10-undecadien-l-ol and 1-decanol as sources of all of the carbons. 

This procedure was used as a key step in the preparation of the sex pheromone from the Douglas fir tussock moth. 

The eutectic mixture AlCls-NaCl-KCl has been found to be a superior catalyst to AICI3 alone, in the Lewis acid-catalysed ene reaction of methyl acrylate with terminal olefins. Hence an 86 14 mixture of geometrical isomers of (4) is obtained from octene the ester (4) is a useful intermediate in the synthesis of the sex pheromone from the Douglas Fir Tussock moth, and of its biologically active isomer. ... 

Figure 3.23 Further examples of lepidopteran sex pheromones. These substances are all produced by adult females to attract males. In many cases the effective pheromone consists of a mixture of compounds, often isomers or homologues. Disparlure, the pheromone of the gypsy moth Lymantria dispar has a branched chain which starts with an isobutyric acid unit and is extended with acetic acid units. The three C2, unsaturated ketones are the pheromone of the Douglas-fir tussock moth Orgya pseudotsuga...

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). 

Z)-l,6-Heneicosadien-ll-one (629), an attractive analog of the Douglas fir tussock moth (Orgyia pseudotsugata) sex pheromone 580) has been identified and synthesized by Smith et al. 652). 

Sower, L. L., and G. E. Daterman Evaluation of synthetic sex pheromone as a control agent for Douglas-fir tussock moth. Envir. Entomol. 6, 889—892 (1977). 

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