Flexible approach for the asymmetric synthesis of (−)-hyacinthacine A1 and its 7a-epimer |
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| Authors: | Chang-Mei Si Zhuo-Ya Mao Rong-Guo Ren Zhen-Ting Du Bang-Guo Wei |
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| Institution: | 1. College of Science, Northwest Agriculture and Forestry University, Yangling, Shaanxi Province 712100, China;2. Department of Chemistry and Institutes of Biomedical Sciences, Fudan University, 220 Handan Road, Shanghai 200433, China |
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| Abstract: | The diastereoselective nucleophilic addition of organic boronic ester to 3-hydroxy-2-substituted N-acyliminium ions 9 led to the formation of 2,5-cis-pyrrolidine 10, from which a convenient synthesis of (−)-7a-epi-1 was developed. In addition, an efficient asymmetric synthesis of (−)-hyacinthacine A1 1 was achieved through the reduction/ring-opening process. |
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| Keywords: | Lactam Nucleophilic addition Asymmetric synthesis Alkaloid Hyacinthacine |
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