首页|Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

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As one of the most common structural motifs in natural products,cyclopentenones usually can be fabricated by Nazarov cyclization using divinyl ketones or functionalized tertiary divinyl carbinols(TDCs)as substrates.However,straightforward method for trans-forming unfunctionalized TDCs to their corresponding cyclopentenones is currently lacking.Herein,we wish to report the total syn-theses of four structurally distinct terpenoids,namely laurane-type marine sesquiterpenoids isolaurene,debromoaplysin and aplysin,and guaiane sesquiterpenoid guaiadienone A,all using a novel synthetic method,named oxidative Nazarov cyclization,as the key step.This work demonstrated our robust method is suitable for synthesizing various highly substituted cyclopentenones.

Total synthesisSynthetic methodsSesquiterpenoidsOxidative Nazarov reactionElectrocyclizationOxoammonium saltPericyclic reactionAnnulation

Yuye Chen、Wenqing Chen、Zhiting Zhang、Jing Xu

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Shenzhen Grubbs Institute and Department of Chemistry and Guangming Advanced Research Institute 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,Guangdong 518055,China

National Natural Science Foundation of ChinaNational Natural Science Foundation of ChinaNational Natural Science Foundation of ChinaShenzhen Science,Technology and Innovation CommissionShenzhen Key Laboratory of Small Molecule Drug Discovery and SynthesisGuangdong Provincial Key Laboratory of CatalysisGuangdong Innovative ProgramEducation Department of Guangdong Province,Key Research Projects in Colleges and Universities in Guangdong ProvinceShenzhen Nobel Prize Scientists Laboratory ProjectInnovative Team of Universities in Guangdong ProvinceGuangdong Natural Science Foundation

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2024

10.1002/cjoc.202400014

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子：0.848
ISSN：1001-604X
年,卷(期)：2024.42(11)