Tetrahedron

Synthesis of the enantiomers of cis-2-methyl-5-hexanolide, the major component of the sex pheromone of the carpenter bee

K Mori, S Senda

Index: Mori, Kenji; Senda, Shuji Tetrahedron, 1985 , vol. 41, # 3 p. 541 - 546

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Citation Number: 56

Abstract

(2R, 5S)-2-Methyl-5-hexanolide and its antipode were synthesized in highly optically pure state (⩾ 98–99% ee) starting from ethyl (S)-lactate and the enantiomers of methyl β- hydroxyisobutyrate. The specific rotations of our samples were [α] D±91.0-93.5°(CHCl3), while the reported values of the samples prepared by resolution or asymmetric synthesis were±64.5–65.6°.