Stereospecific acyloin ring contraction controlled by glucose and concise total synthesis of saffloneoside
Literature Information
Publication Date
2019-04-11
DOI
10.1039/C9QO00279K
Impact Factor
5.281
Authors
Wan Gao, Jian-Shuang Jiang, Zhong Chen, Ya-Nan Yang, Zi-Ming Feng, Xu Zhang, Xiang Yuan, Pei-Cheng Zhang
View Original
Abstract
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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Organic Chemistry Frontiers
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