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Issue 11, 2019
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Stereospecific acyloin ring contraction controlled by glucose and concise total synthesis of saffloneoside

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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

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Publication details

The article was received on 22 Feb 2019, accepted on 09 Apr 2019 and first published on 11 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00279K
Org. Chem. Front., 2019,6, 1858-1862

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    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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