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Total synthesis of clostrubin
Alternative TitleTotal synthesis of clostrubin
Yang M(阳铭); Li J(李健); Li A(李昂)
Source PublicationNat. Commun.
AbstractClostrubin is a potent antibiotic against methicillin-and vancomycin-resistant bacteria that was isolated from a strictly anaerobic bacterium Clostridium beijerinckii in 2014. This polyphenol possesses a fully substituted arene moiety on its pentacyclic scaffold, which poses a considerable challenge for chemical synthesis. Here we report the first total synthesis of clostrubin in nine steps (the longest linear sequence). A desymmetrization strategy is exploited based on the inherent structural feature of the natural product. Barton-Kellogg olefination forges the two segments together to form a tetrasubstituted alkene. A photoinduced 6p electrocyclization followed by spontaneous aromatization constructs the hexasubstituted B ring at a late stage. In total, 200 mg of clostrubin are delivered through this approach.
Subject Area生命有机化学
Indexed BySCI
WOS IDWOS:000352633900029
Citation statistics
Cited Times:24[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorLi A(李昂)
Affiliation中科院上海有机化学研究所, 生命有机化学国家重点实验室
Recommended Citation
GB/T 7714
Yang M,Li J,Li A. Total synthesis of clostrubin[J]. Nat. Commun.,2015,6:6445.
APA 阳铭,李健,&李昂.(2015).Total synthesis of clostrubin.Nat. Commun.,6,6445.
MLA 阳铭,et al."Total synthesis of clostrubin".Nat. Commun. 6(2015):6445.
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