中国化学快报(英文版)2024,Vol.35Issue(4) :336-339.DOI:10.1016/j.cclet.2023.108733

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

Jingping Hu Jing Xu
中国化学快报(英文版)2024,Vol.35Issue(4) :336-339.DOI:10.1016/j.cclet.2023.108733

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

Jingping Hu 1Jing Xu1
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作者信息

  • 1. 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
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Abstract

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 struc-tures,several contiguous stereogenic centers,and vicinal all-carbon quaternary centers make these al-kaloids 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 cycloiso-merization.In addition,synthesis of a daphnezomine L-type alkaloid,paxdaphnidine A,was also studied.

Key words

Total synthesis/Daphniphyllum alkaloids/Yuzurimine-type alkaloids/Prins reaction/Enyne cycloisomerization

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基金项目

国家自然科学基金(21971104)

国家自然科学基金(22271136)

Shenzhen Key Lab-oratory of Small Molecule Drug Discovery and Synthesis(ZDSYS20190902093215877)

Guangdong Provincial Key Laboratory of Catalysis(2020B121201002)

Guangdong Innovative Pro-gram(2019BT02Y335)

Education Department of Guangdong Province,Key research projects in colleges and universities in Guangdong Province(2021ZDZX2035)

Shenzhen Nobel Prize Scientists Laboratory Project(C17783101)

Innovative Team of Universities in Guangdong Province(2020KCXTD016)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
参考文献量49
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