Daphnezomines A和B的四环核心骨架合成
收稿日期: 2022-08-13
修回日期: 2022-09-02
网络出版日期: 2022-10-10
基金资助
国家自然科学基金(21971104); 广东省教育厅高校重点科研项目(2021ZDZX2035); 深圳湾实验室(SZBL2019062801006); 深圳市诺贝尔奖科学家实验室(C17783101); 广东省本土创新团队项目(2019BT02Y335); 广东省高校创新团队(2020KCXTD016); 广东省催化化学重点实验室(2020B121201002); 深圳市科技创新委员会(ZDSYS20190902093215877)
Synthesis of Tetracyclic Core Structure of Daphnezomines A and B
Received date: 2022-08-13
Revised date: 2022-09-02
Online published: 2022-10-10
Supported by
National Natural Science Foundation of China(21971104); Key Research Projects in Colleges and Universities of Education Department of Guangdong Province(2021ZDZX2035); Shenzhen Bay Laboratory(SZBL2019062801006); Shenzhen Nobel Prize Scientists Laboratory Project(C17783101); Guangdong Innovative Program(2019BT02Y335); Innovative Team of Universities in Guangdong Province(2020KCXTD016); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002); Shenzhen Science and Technology Innovation Committee(ZDSYS20190902093215877)
在虎皮楠生物碱家族中, daphnezomine A型生物碱仅包含三位成员: daphnezomine A (1), daphnezomine B (2)以及dapholdhamine B. 这些生物碱含有独特的氮杂金刚烷骨架, 9个连续的手性立体中心, 因此呈现出巨大的合成挑战性. 报道了分子1和2的四环核心骨架的合成. 关键步骤包括一个黄氏酰胺活化增环反应和一个Hutchins-Kabalka还原重排反应.
胡晶平 , 陈文清 , 蒋宇旸 , 徐晶 . Daphnezomines A和B的四环核心骨架合成[J]. 有机化学, 2023 , 43(1) : 171 -177 . DOI: 10.6023/cjoc202208014
Among the tiniest Daphniphyllum alkaloid subfamilies, daphnezomine A-type alkaloids consist of only three known members, namely daphnezomine A (1), daphnezomine B (2) and dapholdhamine B. These alkaloids contain a unique aza-adamantane core along with nine contiguous stereogenic centers, thus presenting remarkable synthetic challenges. The synthesis of tetracyclic core structure of 1 and 2 was reported. The key steps in our approach include a Huang’s amide-activa tion-annulation and a Hutchins-Kabalka reductive rearrangement.
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