Chinese Journal of Organic Chemistry >
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)
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.
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 . DOI: 10.6023/cjoc202208014
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