Lasioderma serricorne cigarette beetle

Scheme 32 summarizes Matteson s synthesis of serricornin [(4S,6S,7S)-21], the female sex pheromone of the cigarette beetle (Lasioderma serricorne) via boronic esters [55]. Due to the highly stereoselective nature of boronic ester chemistry, this synthesis of 21 was quite efficient. 

Howe, R.W. 1957. A laboratory study of the cigarette beetle, Lasioderma serricorne (F.) (Col., Anobiidae), with a critical review of the literature on its biology. Bull. Entomol. Res. 48, 9-56. 

Attractive Compounds. Only little is known about the systems of chemical communication in anobiid beetles. Investigations have been mainly concerned with two economically important species, the cigarette beetle, Lasioderma serricorne, and the drugstore beetle, Stegobium paniceum. 

Baker, J.E., Sukkestad, D.R., Nelson, D. R. and Fatland, C.L. (1979). Cuticular lipids of larvae and adults of the cigarette beetle, Lasioderma serricorne. Insect Biochem., 9, 603-611. 

Scrricornin (4S.6S.7S) O () [ Cigarette beetle Lasioderma serricorne) Ps Organoborane chcmistiy fl49)... 

Serricornin (113, Figure 4.67) was isolated and identified in 1979 by Chuman et al. in Japan as the female-produced sex pheromone of the cigarette beetle (Lasioderma serricorne), which is a serious pest... 

Tubers (potato, cassava) Araecerus fasciculatusa Lasioderma serricorne Phthorimaea operculellaa Prostephanus truncatusa Coffee bean weevil Cigarette beetle Potato tuber moth Larger grain borer... 

Our recent synthesis of serricomin (17) (8), the pheromone of the cigarette beetle, Lasioderma serricorne, illustrates the efficiency of the method when an optimized stereodirector strategy is employed and all of the substituents are nonpolar (Scheme 3). Because the synthetic method connects a single stereogenic carbon in each chain extension step, the required sequence of linear... 

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