The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.