Many species of pest aphids reproduce sexually on the winter host. The sex pheromone of the vetch aphid, Megoura v i c i a e , has recently been identified as comprising the,(4aS,7S,7aR)-isomers of nepetalactone and nepetalactol. The stereochemistry at carbon-1 of the lactol was not defined, but is now shown, by X-ray crystallography on the 3,5-dinitrobenzoate ester, to have the R configuration, This lactol is the major product from reduction of the lactone with diisobutylaluminium hydride.Results from the similar reduction of other nepetalactone isomers are presented.
Lithiation and alkylation of a 2-isopropylidineaziridine bearing an (S)-alpha-methylbenzyl group on nitrogen proceeds with high levels of diastereocontrol (80-90% de).
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