Asymmetric total synthesis of all four isomers of 6-acetoxy-5-hexadecanolide: the major component of mosquito oviposition attractant pheromones |
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| Institution: | 1. Department of Chemistry, College of Life Sciences and Environment, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, China;2. The Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;1. RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan;2. Department of Chemistry, The Graduate School of Science and Engineering, Tokyo Institute of Technology, Ookayama, Tokyo 152-8551, Japan;3. Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan |
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| Abstract: | An asymmetric total synthesis of (5S,6R)-(+)-erythro-6-acetoxy-5-hexadecanolide 1a has been accomplished from readily available hex-5-yn-1-ol via Shi’s asymmetric epoxidation as the key step, in eight steps with an overall yield of 33.5%. In addition, the stereoselective synthesis of all four isomers of 6-acetoxy-5-hexadecanolide 1a–1d were obtained via Sharpless asymmetric dihydroxylation and Mitsunobu reaction as the key steps with overall yields of 16.5–21.2%, respectively. |
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