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Total Syntheses of Norrisolide-Type Spongian Diterpenes ChelovioleneC, SeconorrisolideB, and SeconorrisolideC
2020-08-10
发表期刊ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (IF:16.1[JCR-2023],16.2[5-Year])
ISSN1433-7851
EISSN1521-3773
发表状态已发表
DOI10.1002/anie.202005600
摘要

The first total syntheses of three unusual norrisolide-type rearranged spongian diterpenes, chelovioleneC, seconorrisolideB, and seconorrisolideC, have been accomplished via a common intermediate through late-stage ring-scissoring. The synthesis features a Wolff ring contraction for the synthesis of the trans-hydrindane system, and a crucial retro Diels-Alder reaction/intramolecular ene cyclization for the rapid stereoselective construction of the furo[2,3-b]furan system, which is commonly seen in rearranged spongian diterpenes.

关键词cyclizations natural products rearrangements terpenoids total synthesis
收录类别SCI ; SCIE ; EI ; IC
语种英语
资助项目National Key Research and Development Program of China[2017YFD0201404] ; National Natural Science Foundation of China[21971122][21772097][21572104]
WOS研究方向Chemistry
WOS类目Chemistry, Multidisciplinary
WOS记录号WOS:000537512100001
出版者WILEY-V C H VERLAG GMBH
WOS关键词ENE REACTION
原始文献类型Article
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文献类型期刊论文
条目标识符https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/121528
专题物质科学与技术学院_PI研究组_梁广鑫组
通讯作者Liang, Guangxin
作者单位
1.Nankai Univ, State Key Lab Elementoorgan Chem, Coll Chem, Tianjin 300071, Peoples R China
2.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
通讯作者单位物质科学与技术学院
推荐引用方式
GB/T 7714
Qiao, Tianjiao,Wang, Yicheng,Zheng, Sujuan,et al. Total Syntheses of Norrisolide-Type Spongian Diterpenes ChelovioleneC, SeconorrisolideB, and SeconorrisolideC[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020.
APA Qiao, Tianjiao,Wang, Yicheng,Zheng, Sujuan,Kang, Huiying,&Liang, Guangxin.(2020).Total Syntheses of Norrisolide-Type Spongian Diterpenes ChelovioleneC, SeconorrisolideB, and SeconorrisolideC.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION.
MLA Qiao, Tianjiao,et al."Total Syntheses of Norrisolide-Type Spongian Diterpenes ChelovioleneC, SeconorrisolideB, and SeconorrisolideC".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020).
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