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

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

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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.

Total synthesisDaphniphyllum alkaloidsYuzurimine-type alkaloidsPrins reactionEnyne cycloisomerization

Jingping Hu、Jing Xu

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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

国家自然科学基金国家自然科学基金Shenzhen Key Lab-oratory of Small Molecule Drug Discovery and SynthesisGuangdong Provincial Key Laboratory of CatalysisGuangdong Innovative Pro-gramEducation Department of Guangdong Province,Key research projects in colleges and universities in Guangdong ProvinceShenzhen Nobel Prize Scientists Laboratory ProjectInnovative Team of Universities in Guangdong Province

2197110422271136ZDSYS201909020932158772020B1212010022019BT02Y3352021ZDZX2035C177831012020KCXTD016

2024

10.1016/j.cclet.2023.108733

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
年,卷(期)：2024.35(4)
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