Enantioselective Total Synthesis of (+)‐Steenkrotin A and Determination of Its Absolute Configuration |
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| Authors: | Saiyong Pan Beiling Gao Jialei Hu Jun Xuan Hujun Xie Prof?Dr Hanfeng Ding |
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| Affiliation: | 1. Department of Chemistry, Zhejiang University, Hangzhou, P.R. China;2. College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, P.R. China |
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| Abstract: | The first enantioselective total synthesis of (+)‐steenkrotin A has been achieved in 18 steps and 4.2 % overall yield. The key features of the strategy entail a Rh‐catalyzed O?H bond insertion followed by an intramolecular carbonyl‐ene reaction, two sequential SmI2‐mediated Ueno–Stork and ketyl–olefin cyclizations, and a cascade intramolecular aldol condensation/vinylogous retro‐aldol/aldol process with inversion of the relative configuration at the C7 position. The absolute configuration of (+)‐steenkrotin A was determined based on the stepwise construction of the stereocenters during the total synthesis. |
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| Keywords: | carbenoids fused-ring systems natural products radical reactions total synthesis |
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