Collect. Czech. Chem. Commun. 2000, 65, 524-538
doi:10.1135/cccc20000524

Versatile Enantioselective Synthesis of Four Diastereomers of Serricornin, a Sex Pheromone of the Cigarette Beetle, Using the SAMP/RAMP-Hydrazone Method

Andreas Job, René Nagelsdiek and Dieter Enders*

Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Strasse 1, D-52074 Aachen, Germany

Abstract

Serricornin is a female-produced sex pheromone of the cigarette beetle (Lasioderma serricorne), which is a pest of dried foodstuffs and tobacco. We report a versatile and short synthesis of all possible 6,7-syn-isomers of serricornin, including the natural isomer. Starting from the SAMP and RAMP derivatives of diethyl ketone we obtained four different enantiopure and diastereomerically pure serricornins. The main advantage of this method is that only a single kind of chiral starting material is needed for the construction of three stereogenic centers. During the synthesis further useful intermediates including (R)- and (S)-1-benzyloxy-2-methylpentan-3-one (4) and (2S,3R)- and (2R,3S)-1-iodo-3-(methoxy- methoxy)-2-methylpentane (9) were obtained.

Keywords: Asymmetric synthesis; Hydrazones; Natural products; Pheromones; Reductions; Total synthesis.

References: 34 live references.