Issue 11, 2019

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
22 Feb 2019
Accepted
09 Apr 2019
First published
11 Apr 2019

Org. Chem. Front., 2019,6, 1858-1862

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

W. Gao, J. Jiang, Z. Chen, Y. Yang, Z. Feng, X. Zhang, X. Yuan and P. Zhang, Org. Chem. Front., 2019, 6, 1858 DOI: 10.1039/C9QO00279K

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