Versatile enantioselective synthesis of four diastereomers of serricornin,a sex pheromone of the cigarette beetle, using the SAMP/RAMP-hydrazone method

Serricornin is a female-produced sex pheromone of the cigarette beetle (Las ioderma serricorne), which is a pest of dried foodstuffs and tobacco. We re port a versatile and short synthesis of all possible 6,7-syn-isomers of ser ricornin, including the natural isomer. Starting from the SAMP and RAMP der ivatives of diethyl ketone eve obtained four different enantiopure and dias tereomerically pure serricornins. The main advantage of this method is that only a single kind of chiral starting material is needed for the construct ion of three stereogenic centers. During the synthesis further useful inter mediates including (R)- and (S)-1-benzyloxy-2-methylpentan-3-one (4) and (2 S,3R)- and (2R,3S)-1-iodo-3-(methoxy-methoxy)-2-methylpentane (9) were obta ined.