Total synthesis of (3Z,9Z,6S,7R) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadienes |
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| Authors: | Kai Xu Shuai Zhao Ming-Wei Shan Jia-Li Yu Yu-Bo Wang |
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| Affiliation: | 1. School of Pharmaceutical and Life Sciences, Changzhou University, Changzhou, Jiangsu, P. R. China;2. Changzhou Nimrod Biotech Inc., Changzhou, Jiangsu, P. R. China |
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| Abstract: | (3Z,9Z,6S,7R)-6,7-epoxy-3,9-octadecadiene (1) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadiene (2) have been stereoselectively synthesized in eight steps from 2-pentyn-1-ol with an overall yield of 8%. The key steps involved the Sharpless asymmetric dihydroxylation of (2E)-oct-2-en-5-yn-1-ol (6). The new synthetic method is suitable for multigram-scale preparation of 1 and 2 and might be used for producing sufficient quantities of the sex pheromone components for management of the pest of tea plantations. |
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| Keywords: | (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadiene sex pheromone sharpless asymmetric dihydroxylation synthesis |
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