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学科主题: 生命有机化学
题名: Total synthesis of clostrubin
其他题名: Total synthesis of clostrubin
作者: Yang M(阳铭); Li J(李健); Li A(李昂)
通讯作者: 李昂
刊名: Nat. Commun.
发表日期: 2015
DOI: 10.1038/ncomms7445
卷: 6, 页:6445
收录类别: SCI
文章类型: 论文
英文摘要: Clostrubin 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.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000352633900029
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/39499
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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作者单位: 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:
Yang M,Li J,Li A. Total synthesis of clostrubin[J]. Nat. Commun.,2015,6:6445.
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