Total Syntheses of Periconiasins A–E |
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| Authors: | Chong Tian Xiaoqiang Lei Yuanhao Wang Zhen Dong Prof?Dr Gang Liu Prof?Dr Yefeng Tang |
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| Affiliation: | 1. School of Pharmaceutical Sciences & Comprehensive AIDS Research Center, Tsinghua University, Beijing, China;2. Tsinghua-Peking Center for Life Sciences, School of Life Sciences, Tsinghua University, Beijing, P.R. China;3. Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu, China |
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| Abstract: | The first and collective total syntheses of periconiasins A–E, a group of naturally occurring cytochalasans, were achieved by a series of rationally designed or bioinspired transformations. Salient features of the syntheses include a tandem aldol condensation/Grob fragmentation to assemble the linear polyketide–amino acid hybrid precursor, a Diels–Alder macrocylization to construct the 9/6/5 tricyclic core of periconiasins A–C, and a transannular carbonyl–ene reaction to forge the polycyclic framework of periconiasins D and E. |
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| Keywords: | biomimetic synthesis cycloaddition natural products polyketides total synthesis |
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