Fu Junkai, Gu Yueqing, Yuan Hao, Luo Tuoping, Liu Song, Lan Yu, Gong Jianxian, Yang Zhen
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science (BNLMS) and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.
Nat Commun. 2015 Oct 16;6:8617. doi: 10.1038/ncomms9617.
The development of an efficient diastereoselective synthesis of the oxabicyclo[3.2.1]octane ring system bearing two oxygenated quaternary chiral centres represents a significant challenge. This motif can be found in a wide range of natural products with significant biological activities. Here we report the synthesis of such kind of scaffold using a cyclohexane-trans-1,4-diol with an alkyne side chain in the presence of Au(I) catalyst. This is a domino process in which two C-H, two C-O and one C-C bond is assembled through a sequence of cyclization/semi-pinacol rearrangements. This strategy has been successfully applied to the asymmetric formal total synthesis of (+)-cortistatins.
高效非对映选择性合成带有两个含氧季碳手性中心的氧杂双环[3.2.1]辛烷环系是一项重大挑战。这种结构单元存在于众多具有显著生物活性的天然产物中。在此，我们报道了在金（I）催化剂存在下，使用带有炔烃侧链的环己烷 - 反式 -1,4 - 二醇合成此类骨架的方法。这是一个多米诺过程，其中通过一系列环化/半频哪醇重排组装了两个C - H键、两个C - O键和一个C - C键。该策略已成功应用于（+） - 皮质抑素的不对称形式全合成。
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