Synthesis of the enantiomers of cis-2-methyl-5-hexanolide,the major component of the sex pheromone of the carpenter bee |
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Authors: | Kenji Mori Shuji Senda |
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Institution: | Department of Agricultural Chemistry, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113 Japan |
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Abstract: | (2R,5S)-2-Methyl-5-hexanolide and its antipode were synthesized in highly optically pure state (?98–99% e.e.) 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°. |
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