title: Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide.
abstract: 6-Acetoxy-5-hexadecanolide (Ia) in the oviposition attractant pheromone released from egg apical droplets of the mosquitoCulex pipiens fatigans Wied. is shown to be the (-)-(5R,6S)- enantiomer. Identification was by chromatography of the 6-trifluoroacetoxy derivatives of the natural pheromone and of the synthetic (-)-(5R,6S)- (Ib) and (+)-(5S,6R)- (IIb) enantiomers on a capillary column having a chiral stationary phase comprising a derivative of (1S,3S)-chrysanthemic acid. The synthetic (-)-(5R,6S)- enantiomer (Ia) attracted oviposition of four fold more mosquito egg rafts than the control (P < 0.01) whereas for the (5S,6R)- enantiomer (IIa) there was no statistically significant oviposition attraction.
authors: London School of Hygiene and Tropical Medicine, WCIE 7HT, London, UK.
authors: B R
authors: BR
authors: Laurence
authors: K
authors: K
authors: Mori
authors: T
authors: T
authors: Otsuka
authors: J A
authors: JA
authors: Pickett
authors: L J
authors: LJ
authors: Wadhams