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

KN Prokhorevich, OG Kulinkovich

Index: Prokhorevich, Konstantin N.; Kulinkovich, Oleg G. Tetrahedron Asymmetry, 2006 , vol. 17, # 21 p. 2976 - 2980

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Citation Number: 10

Abstract

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-γ-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)- ...