Stereospecific acyloin ring contraction controlled by glucose and concise total synthesis of saffloneoside
文献信息
发布日期
2019-04-11
DOI
10.1039/C9QO00279K
影响因子
5.281
作者
Wan Gao, Jian-Shuang Jiang, Zhong Chen, Ya-Nan Yang, Zi-Ming Feng, Xu Zhang, Xiang Yuan, Pei-Cheng Zhang
查看原文
摘要
Saffloneoside (1), a structurally unusual p-hydroxycinnamylcyclopentenone C-glucoside obtained from the florets of Carthamus tinctorius, was synthesized on a gram scale in seven steps. A stereospecific acyloin ring contraction controlled by the chirality of glucose moiety at the C5 position of highly substituted cyclohexadienones was discovered. The possible β-orientation hydrogen migration mechanism in the transformation of C5(sp2) into C5(sp3) was proposed.
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NDT & E International
Bioorganic & Medicinal Chemistry Letters
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Polycyclic Aromatic Compounds
Biocatalysis and Biotransformation
Cellulose
Atomization and Sprays
Critical Reviews in Solid State and Materials Sciences
Bioorganic & Medicinal Chemistry
Herald of the Russian Academy of Sciences
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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