Asymmetric Synthesis of the Tricyclic Core of Calyciphylline A-Type Alkaloids via Intramolecular [3+2] Cycloaddition
Wang, Lu1; Xu, Chen1; Chen, Li1; Hao, Xiaojiang2; Wang, David Zhigang1
2014-02-21
发表期刊ORGANIC LETTERS
ISSN1523-7060
卷号16期号:4页码:1076-1079
摘要Asymmetric synthesis of the [5-6-7] tricyclic system common to the Calyciphylline A-type alkaloids is reported, featuring Overman rearrangement, Heck cyclization, intramolecular [3 + 2] cycloaddition, diastereoselective hydrogenation, and Claisen rearrangement as strategic events. The approach is capable of installing the crucial carbonyl functionality as well as multiple stereogenic centers within a congested polycyclic ring skeleton.
关键词Beta-hydroxy Ketones Nitrile Oxide Cycloaddition Daphniphyllum Alkaloids Tetracyclic Core Daphnilactone-b Ring-system Construction Reduction Delta-2-isoxazolines Route
资助信息National Science Foundation of China [21290183, 21272014, 20972008, 20672160]; national "973 Project" of the State Ministry of Science and Technology [2012CB722602, 2010CB833200]; Shenzhen Bureau of Science and Technology
学科领域Chemistry, Organic
DOI10.1021/ol403609c
收录类别SCI ; IC
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000331926800012
引用统计
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/17942
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, Kunming 650204, Peoples R China
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Wang, Lu,Xu, Chen,Chen, Li,et al. Asymmetric Synthesis of the Tricyclic Core of Calyciphylline A-Type Alkaloids via Intramolecular [3+2] Cycloaddition[J]. ORGANIC LETTERS,2014,16(4):1076-1079.
APA Wang, Lu,Xu, Chen,Chen, Li,Hao, Xiaojiang,&Wang, David Zhigang.(2014).Asymmetric Synthesis of the Tricyclic Core of Calyciphylline A-Type Alkaloids via Intramolecular [3+2] Cycloaddition.ORGANIC LETTERS,16(4),1076-1079.
MLA Wang, Lu,et al."Asymmetric Synthesis of the Tricyclic Core of Calyciphylline A-Type Alkaloids via Intramolecular [3+2] Cycloaddition".ORGANIC LETTERS 16.4(2014):1076-1079.
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