Daphnezomines A和B的四环核心骨架合成

doi:10.6023/cjoc202208014

有机化学 ›› 2023, Vol. 43 ›› Issue (1): 171-177.DOI: 10.6023/cjoc202208014 上一篇下一篇

研究论文

Daphnezomines A和B的四环核心骨架合成

胡晶平^a^,^b, 陈文清^b, 蒋宇旸^b, 徐晶^b^,^c^,^*()

a 哈尔滨工业大学化工与化学学院哈尔滨 150001
b 南方科技大学化学系与格拉布斯研究院广东省催化化学重点实验室深圳市小分子药物发现与合成重点实验室广东深圳 518055
c 深圳湾实验室广东深圳 518132

收稿日期:2022-08-13 修回日期:2022-09-02 发布日期:2022-10-10
通讯作者: 徐晶
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

Jingping Hu^a^,^b, Wenqing Chen^b, Yuyang Jiang^b, Jing Xu^b^,^c()

a School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001
b Department of Chemistry and Shenzhen Grubbs Institute Guangdong Provincial Key Laboratory of Catalysis Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Southern University of Science and Technology, Shenzhen, Guangdong 518055
c Shenzhen Bay Laboratory, Shenzhen, Guangdong 518132

Received:2022-08-13 Revised:2022-09-02 Published:2022-10-10
Contact: Jing Xu
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)

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摘要/Abstract

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.

关键词: 全合成, 虎皮楠生物碱, daphnezomine A, daphnezomine B, 氮杂金刚烷, 黄氏酰胺活化增环反应, Hutchins-Kabalka还原重排

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.

Key words: total synthesis, Daphniphyllum alkaloids, daphnezomine A, daphnezomine B, aza-adamantane, Huang' s amide-activation-annulation, Hutchins-Kabalka reductive rearrangement

引用此文

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.

Jingping Hu, Wenqing Chen, Yuyang Jiang, Jing Xu. Synthesis of Tetracyclic Core Structure of Daphnezomines A and B[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 171-177.

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图/表 4

Figure 1. Daphnezomine A-type alkaloids

Scheme 1. Retrosynthetic analysis of 1and 2.

Scheme 2. Synthesis of the tetracyclic core of 1 and 2

Scheme 3. Plausible pathway for the formation of 14.

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Daphnezomines A和B的四环核心骨架合成

Synthesis of Tetracyclic Core Structure of Daphnezomines A and B

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