A practical total synthesis of (+)-isogalbulin and (+)-galbulin |
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| Authors: | Xiaoyu Li Xiaozhen JiaoXiaoyu Liu Chengsen TianLiang Dong Yangyang YaoPing Xie |
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| Affiliation: | State Key Laboratory of Bioactive Substance and Function of Natural Medicine, Beijing Key Laboratory of Active Substance Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, No. 1, Xiannongtan St., Beijing 100050, China |
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| Abstract: | A practical total synthesis of the natural products (+)-isogalbulin and (+)-galbulin has been achieved in 10 steps from readily available 3-(3,4-dimethoxyphenyl)propanoic acid. The total yields were 12.3% and 12.9%, respectively. The key steps involved Evans asymmetric alkylation, Sharpless asymmetric epoxidation, and a highly regioselective opening of 1-benzyloxy-2,3-epoxides with an organoaluminum ate-complex formed by Me3Al and n-BuLi. |
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| Keywords: | (+)-Isogalbulin (+)-Galbulin Evans asymmetric alkylation Sharpless asymmetric epoxidation Bimolecular nucleophilic substitution |
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