Citation: Jingping Hu, Jing Xu. Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H[J]. Chinese Chemical Letters, ;2024, 35(4): 108733. doi: 10.1016/j.cclet.2023.108733 shu

Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H

Jingping Hu ,
Jing Xu ^*,

Shenzhen Grubbs Institute and Department of Chemistry and Guangdong Provincial Key Laboratory of Catalysis and Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Southern University of Science and Technology, Shenzhen 518055, China

xuj@sustech.edu.cn

Received Date: 12 May 2023
Revised Date: 15 June 2023
Accepted Date: 25 June 2023
Available Online: 28 June 2023

Figures(3)

One of the largest subfamilies within the famous Daphniphyllum alkaloid family is made up of the yuzurimine-type (or macrodaphniphyllamine-type) alkaloids. Their complex aza-polycyclic caged structures, several contiguous stereogenic centers, and vicinal all-carbon quaternary centers make these alkaloids formidable challenge for synthetic chemists. Recently, synthesis of these alkaloids has received extensive attention from our community. Herein, we wish to report the total synthesis of C₁₄–epi-deoxycalyciphylline H, a putative member of yuzurimine-type alkaloid subfamily. Key transformations employed in our approach include an intramolecular Prins reaction and a Pd-catalyzed enyne cycloisomerization. In addition, synthesis of a daphnezomine L-type alkaloid, paxdaphnidine A, was also studied.
- Total synthesis,
- Daphniphyllum alkaloids,
- Yuzurimine-type alkaloids,
- Prins reaction,
- Enyne cycloisomerization
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Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C14–epi-deoxycalyciphylline H

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通讯作者: 陈斌, bchen63@163.com

Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H