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题名: Tandem rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction for the construction of linear triquinane skeleton: Total syntheses of (+/-)-hirsutene and (+/-)-1-desoxyhypnophilin
作者: Jiao, Lei1;  Yuan, Changxia1;  Yu, Zhi-Xiang1
刊名: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
发表日期: 2008-04-02
DOI: 10.1021/ja7100449
卷: 130, 期:13, 页:4421-4430
收录类别: SCI ;  IC ;  CCR
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
英文摘要: A tandem reaction involving a Rh(I)-catalyzed two-component [(5+2)+1] cycloaddition and an aldol condensation has been developed to construct the tricyclo[6.3.0.0(2,6)]undecane skeleton and its heteroatom-imbedded analogues. Meanwhile, this method has been successfully applied to natural product synthesis for the first time. The present strategy enables a straightforward approach to the natural linear triquinane skeleton, as demonstrated by concise and step economical syntheses of hirsutene and 1-desoxyhypnophilin, whereby the linear triquinane core is diastereoselectively established in one manipulation with correct placement of all stereocenters, including two quarternary centers. This first application of the Rh(I)-catalyzed [(5+2)+1] cycloaddition in natural product synthesis highlights the efficiency of this methodology for constructing complex fused ring systems.
关键词[WOS]: CATALYZED 5+2 CYCLOADDITION ;  ASYMMETRIC TOTAL-SYNTHESIS ;  3-COMPONENT CYCLOADDITIONS ;  NATURAL-PRODUCTS ;  IDEAL SYNTHESIS ;  HIRSUTENE ;  VINYLCYCLOPROPANES ;  (&/-)-HIRSUTENE ;  REARRANGEMENT ;  METATHESIS
语种: 英语
WOS记录号: WOS:000254549000043
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/140754
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Engn,Coll Chem, Beijing 100871, Peoples R China

Recommended Citation:
Jiao, Lei,Yuan, Changxia,Yu, Zhi-Xiang. Tandem rh(I)-catalyzed [(5+2)+1] cycloaddition/aldol reaction for the construction of linear triquinane skeleton: Total syntheses of (+/-)-hirsutene and (+/-)-1-desoxyhypnophilin[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2008,130(13):4421-4430.
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