Synthetic Strategies Towards the Sex Pheromone of Trogoderma Species
DOI:
https://doi.org/10.12970/2308-8044.2015.03.01.1Keywords:
sex pheromones, trogoderma, total synthesis.Abstract
Z-14-methyl-8-hexadecenal and its E-isomer were identified as the essential female secreted sex pheromones of trogoderma species of insects. Since the discloser of its structure in 1969, (Z)-(-)-14-methyl-8-hexadecen-l-ol and methyl (E)-(-)-14-methyl-8-hexadecenoate as the sex pheromones have been the subject of intense study by the synthetic organic community. Several strategies have been developed for the total synthesis of these exciting pheromone molecules and they are discussed in detail.
References
Rodin JO, Silverstein RM, Burkholder WE, Gorman JE. Sex Attractant of the Black Carpet Beetle. Science 1969; 165: 904. http://dx.doi.org/10.1126/science.165.3896.904
Cross JH, Byler RC, Cassidy RF, Jr Silverstein RM, Greenblatt RE, Burkholder WE, Levinson AR, Levinson HZJ. Porapak-Q collection of pheromone components and isolation of (Z)- and (E)-14-methyl-8-hexadecenal, sex pheromone components, from the females of four species of Trogoderma (Coleoptera: Dermestidae). Chem Ecol 1976; 2: 457. http://dx.doi.org/10.1007/BF00988811
Mori K. Absolute configuration of (-)-14-methyl-cis-8-hexadecen-1-ol and methyl (-)-14-methyl-cis-8-hexadecenoate, the sex attractant of female dermestid beetle, trogoderma inclusum le conte. Tetrahedron Lett 1973; 14: 3869. http://dx.doi.org/10.1016/S0040-4039(01)87060-X
(a) Mori K. Absolute configurations of (−)-14-methylhexadec-8-cis-en-1-ol and methyl (−)-14-methylhexadec-8-cis-enoate, the sex pheromone of female dermestid. Tetrahedron 1974; 30: 3817. http://dx.doi.org/10.1016/S0040-4020(01)97069-3
(b) Suguro T, Mori K. Synthesis and biological activity of both (E)- and (Z)-isomers of optically pure (S)-14-methyl-8-hexadecenal (trogodermal), the antipodes of the pheromone of the khapra beetle. Agric Biol Chem 1979; 43: 409. http://dx.doi.org/10.1271/bbb1961.43.409
(c) Mori K, Kuwahara S, Levinson HZ, Levinson AR. Synthesis and biological activity of both (E)- and (Z)-isomers of optically pure (S)-14-methyl-8-hexadecenal (trogodermal), the antipodes of the pheromone of the khapra beetle. Tetrahedron 1982; 38: 2291. http://dx.doi.org/10.1016/0040-4020(82)87005-1
Mori K. Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group. Tetrahedron 2009; 65: 3900. http://dx.doi.org/10.1016/j.tet.2009.02.064
Rossi R, Carpita A. Insect pheromones: Synthesis of chiral sex pheromone components of several species of trogoderma (coleoptera: dermestidae). Tetrahedron 1977; 33: 2447. http://dx.doi.org/10.1016/0040-4020(77)80262-7
Rossi R, Salvadori PA, Carpita A, Niccoli A. Synthesis of the (-) enantiomers of the pheromone components of several species of trogoderma [coleoptera: dermestidae. Tetrahedron 1979; 35: 2039. http://dx.doi.org/10.1016/S0040-4020(01)88975-4
Yadav JS, Chandravathi Ch, Thrimurtulu N, Prasad AR, Al Ghamdi A. A Practical Total Synthesis of Both E- and Z-Isomers of Optically Pure (S)-14-Methylhexadec-8-enal (Trogodermal). Synthesis 2013; 45: 1513. http://dx.doi.org/10.1055/s-0033-1338432
Yadav JS, Venkatesh M, Thrimurtulu N, Prasad AR. Stereoselective Synthesis of (-)-PF1163A via Prins Cyclization. Synlett 2010; 1255. http://dx.doi.org/10.1055/s-0029-1219839
Corey EJ, Fuchs PLA. Synthetic method for formyl→ethynyl conversion (RCHO→RCOCH or RCOCR′). Tetrahedron Lett 1972; 13: 3769. http://dx.doi.org/10.1016/S0040-4039(01)94157-7
