A new synthesis of tanikolide |
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| Authors: | Hongbin Zhai Qingshou ChenJingrui Zhao Shengjun LuoXueshun Jia |
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| Affiliation: | a Laboratory of Modern Synthetic Organic Chemistry and State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
b Department of Chemistry, Shanghai University, Shanghai 200436, China |
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| Abstract: | We report a concise synthesis of tanikolide 1, which was obtained from ethyl 2-oxocyclopentanecarboxylate in four steps: alkylation, Baeyer-Villiger reaction, saponification, and reduction/lactonization, in 70% overall yield. Our strategy should be suitable for the preparation of 1 in multigram or larger quantities. The net result of the last two steps (i.e. saponification and reduction/lactonization) is an efficient reduction of the ethoxycarbonyl of 3 while keeping the lactone carbonyl intact. |
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| Keywords: | tanikolide synthesis marine natural products |
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