Stegobium paniceum pheromone

Kuwahara, Y., Fukami, H., Ishii, S., Matsumura, F. and Burkholder, W. E. (1975b). Studies on the isolation and bioassay of the sex pheromone of the drugstore beetle, Stegobium paniceum (Coleoptera Anobiidae). Journal of Chemical Ecology 1 413 122. 

Chemical studies on the Anobiidae sex pheromone of the drugstore beetle, Stegobium paniceum (L) (Coleoptera). Tetrahedron 34 1769-1774. 

Figure 6.6 Structures of 2,3-dihydro-2,3,5-trimethyl-6-(1 -methyl-2 -oxobutyl)-4H-pyran-4-one (stegobinone), pheromone of Stegobium paniceum (L.) (Anobiidae) (Kuwahara et al., 1978) and (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene, pheromone component of Carpophilus hemipterus (L.) (Nitidulidae) (Bartelt et al., 1991). The carbon skeletons are identical, and likely derived through similar pathways (see text).

Strong protic acids will also cleave benzyl ethers. A highly stereoselective synthesis of the sex pheromone of the drugstore beetle Stegobium paniceum by Matteson and co-workers277 conveniently accomplished the debenzylation of the benzyl ether 151.1 with methanesulfonic add in chloroform [Scheme 4.151]. 

Drugstore beetle (Stegobium paniceum) is a serious pest of a wide variety of commodities and stored products. In 1978 Y. Kuwahara et al. proposed the structure of stegobinone, the major and crystalline component of the female-produced sex pheromone of 5. paniceum, as 114 (Figure 4.69). Nothing was... 

The pheromone components of C. lugubris and C. hemipterus are undoubtedly related bios3mthetically. Although none of these compounds had been known prior to the nitidulid research, the 13-carbon pheromone component 1 of C. hemipterus has the same carbon skeleton as the pheromone of the drugstore beetle, Stegobium paniceum (14). A polyketide origin of this pheromone was proposed, in which the polyketide arose from the condensation of one acetate and four propionate units (L5). Polyketide biosyntheses have also been proposed for a number of related structures (16, 17). The... 

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