The first convergent total synthesis of penarolide sulfate A2, a novel α-glucosidase inhibitor?
Organic & Biomolecular Chemistry Pub Date: 2014-01-22 DOI: 10.1039/C3OB42364F
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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