Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Chen，Yuye; Chen，Wenqing; Zhang，Zhiting; Xu，Jing

2024-06-01

10.1002/cjoc.202400014

Chinese Journal of Chemistry   影响因子和分区

1001-604X

1614-7065

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 transforming unfunctionalized TDCs to their corresponding cyclopentenones is currently lacking. Herein, we wish to report the total syntheses 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.

Annulation Electrocyclization Oxidative Nazarov reaction Oxoammonium salt Pericyclic reaction Sesquiterpenoids Synthetic methods Total synthesis

SCI

英语

第一 ; 通讯

CHEMISTRY

2-s2.0-85185934488

Scopus

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

Chen，Yuye,Chen，Wenqing,Zhang，Zhiting,et al. Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction[J]. Chinese Journal of Chemistry,2024,42(11):1267-1274.

Chen，Yuye,Chen，Wenqing,Zhang，Zhiting,&Xu，Jing.(2024).Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction.Chinese Journal of Chemistry,42(11),1267-1274.

Chen，Yuye,et al."Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction".Chinese Journal of Chemistry 42.11(2024):1267-1274.