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Discovery and bioinspired total syntheses of unprecedented sesquiterpenoid dimers unveiled bifurcating [4+2] cycloaddition and target differentiation of enantiomers
He, Tao-Bin; Yan, Bing-Chao; Zhou, Yuan-Fei; Sang, Yue-Qian; Li, Xiao-Nian; Sun, Han-Dong; Wang, Chu; Xue, Xiao-Song; Puno, Pema-Tenzin
2024
Source PublicationCHEMICAL SCIENCE
Volume15Issue:4
Abstract[4 + 2] cycloaddition has led to diverse polycyclic chiral architectures, serving as novel sources for organic synthesis and biological exploration. Here, an unprecedented class of cadinane sesquiterpene [4 + 2] dimers, henryinins A-E (1-5), with a unique 6/6/6/6/6-fused pentacyclic system, were isolated from Schisandra henryi. The divergent total syntheses of compounds 1-5 and their enantiomers (6-10) were concisely accomplished in eight linear steps using a protection-free approach. Mechanistic studies illustrated the origin of selectivity in the key [4 + 2] cycloaddition as well as the inhibition of reaction pathway bifurcation via desymmetrization. The chemical proteomics results showed that a pair of enantiomers shared common targets (PRDX5 C100 and BLMH C73) and had unique targets (USP45 C588 for 4 and COG7 C419 for 9). This work provides experimental evidence for the discovery of unprecedented cadinane dimers from selective Diels-Alder reaction and a powerful strategy to explore the biological properties of natural products. The [4 + 2] cycloaddition has led to diverse polycyclic chiral architectures, serving as novel sources for organic synthesis and biological exploration.
KeywordDIELS-ALDER REACTION BIOMIMETIC SYNTHESES EFFICIENT ACCESS DEHYDROGENATION CYCLOHEXANONES BIOSYNTHESIS CONVERSION OXIDATION DYNAMICS PHENOLS
Subject AreaChemistry
DOI10.1039/d3sc05233h
WOS IDWOS:001113043300001
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Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/74883
Collection中国科学院昆明植物研究所
Recommended Citation
GB/T 7714
He, Tao-Bin,Yan, Bing-Chao,Zhou, Yuan-Fei,et al. Discovery and bioinspired total syntheses of unprecedented sesquiterpenoid dimers unveiled bifurcating [4+2] cycloaddition and target differentiation of enantiomers[J]. CHEMICAL SCIENCE,2024,15(4).
APA He, Tao-Bin.,Yan, Bing-Chao.,Zhou, Yuan-Fei.,Sang, Yue-Qian.,Li, Xiao-Nian.,...&Puno, Pema-Tenzin.(2024).Discovery and bioinspired total syntheses of unprecedented sesquiterpenoid dimers unveiled bifurcating [4+2] cycloaddition and target differentiation of enantiomers.CHEMICAL SCIENCE,15(4).
MLA He, Tao-Bin,et al."Discovery and bioinspired total syntheses of unprecedented sesquiterpenoid dimers unveiled bifurcating [4+2] cycloaddition and target differentiation of enantiomers".CHEMICAL SCIENCE 15.4(2024).
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