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Issue 13, 2014
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The first convergent total synthesis of penarolide sulfate A2, a novel α-glucosidase inhibitor

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Abstract

Penarolide sulfate A2, a 31-membered macrolide encompassing a proline residue and three sulfate groups, was firstly synthesized in 16 linear steps with 4.8% overall yield. Three consecutive stereogenic centers in penarolide sulfate A2 were efficiently derived from natural chiral template L-arabinose. The crucial assembly reactions included Brown asymmetric allylation, olefin cross-metathesis, alkyne-epoxide coupling, and macrolactamization. The anti-yeast α-glucosidase activities of penarolide sulfate A2 and its fully desulfated derivative were examined showing IC50 values of 4.87 and 10.74 μg mL−1, respectively.

Graphical abstract: The first convergent total synthesis of penarolide sulfate A2, a novel α-glucosidase inhibitor

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Publication details

The article was received on 26 Nov 2013, accepted on 19 Jan 2014 and first published on 22 Jan 2014


Article type: Paper
DOI: 10.1039/C3OB42364F
Citation: Org. Biomol. Chem., 2014,12, 2071-2079
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    The first convergent total synthesis of penarolide sulfate A2, a novel α-glucosidase inhibitor

    Y. Gao, Q. Shan, J. Liu, L. Wang and Y. Du, Org. Biomol. Chem., 2014, 12, 2071
    DOI: 10.1039/C3OB42364F

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