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ShanghaiTech University Knowledge Management System
A Concise Formal Synthesis of (-)-Hamigeran B | |
2013-02-15 | |
发表期刊 | ORGANIC LETTERS (IF:4.9[JCR-2023],4.5[5-Year]) |
ISSN | 1523-7060 |
卷号 | 15期号:4页码:871-873 |
发表状态 | 已发表 |
DOI | 10.1021/ol400030a |
摘要 | A concise and efficient formal synthesis of (-)-hamigeran B is reported. The critical intermediate was synthesized from 3-methoxy-5-methylphenyl trifluoromethanesulfonate with an 11-steps 7.2% total yield route. The chiral quaternary carbon was efficiently and steroselectively constructed through an intermolecular Pauson-Khand reaction and a Claisen rearrangement reaction with >99% ee; the cyclohexane B was then closed through an aldehyde Friedel Crafts cyclization. Lastly, the isopropenyl group of ring C was introduced through a Suzuki coupling reaction. |
收录类别 | SCI ; IC ; CCR |
语种 | 英语 |
资助项目 | Science and Technology Commission of Shanghai Municipality[12DZ1930902] |
WOS研究方向 | Chemistry |
WOS类目 | Chemistry, Organic |
WOS记录号 | WOS:000315254500039 |
出版者 | AMER CHEMICAL SOC |
WOS关键词 | OXIDATIVE KINETIC RESOLUTION ; PAUSON-KHAND REACTION ; HYDROXY-O-QUINODIMETHANES ; AEROBIC ALCOHOL OXIDATIONS ; SECONDARY ALCOHOLS ; HAMIGERAN-B ; VINYL TRANSETHERIFICATION ; CLAISEN REARRANGEMENT ; ASYMMETRIC-SYNTHESIS ; MOLECULAR-OXYGEN |
原始文献类型 | Article |
引用统计 | 正在获取...
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文献类型 | 期刊论文 |
条目标识符 | https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/2458 |
专题 | 免疫化学研究所 免疫化学研究所_特聘教授组_抗体化学实验室 |
通讯作者 | Jiang, Biao |
作者单位 | 1.Chinese Acad Sci, Shanghai Inst Organ Chem, CAS Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China 2.Chinese Acad Sci, Shanghai Adv Res Inst, Shanghai 201210, Peoples R China 3.ShanghaiTech Univ, Shanghai Inst Adv Immunochem Studies, Shanghai 201210, Peoples R China |
第一作者单位 | 免疫化学研究所 |
通讯作者单位 | 免疫化学研究所 |
推荐引用方式 GB/T 7714 | Jiang, Biao,Li, Ming-ming,Xing, Ping,et al. A Concise Formal Synthesis of (-)-Hamigeran B[J]. ORGANIC LETTERS,2013,15(4):871-873. |
APA | Jiang, Biao,Li, Ming-ming,Xing, Ping,&Huang, Zuo-gang.(2013).A Concise Formal Synthesis of (-)-Hamigeran B.ORGANIC LETTERS,15(4),871-873. |
MLA | Jiang, Biao,et al."A Concise Formal Synthesis of (-)-Hamigeran B".ORGANIC LETTERS 15.4(2013):871-873. |
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