Stereospecific acyloin ring contraction controlled by glucose and concise total synthesis of saffloneoside

文献情報

出版日 2019-04-11

DOI 10.1039/C9QO00279K

インパクトファクター 5.281

著者

Wan Gao, Jian-Shuang Jiang, Zhong Chen, Ya-Nan Yang, Zi-Ming Feng, Xu Zhang, Xiang Yuan, Pei-Cheng Zhang

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 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

Stereospecific acyloin ring contraction controlled by glucose and concise total synthesis of saffloneoside

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