Practical Synthesis of Bredemolic Acid, a Natural Inhibitor of Glycogen Phosphorylase
- 11 October 2008
- journal article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 71 (11), 1877-1880
- https://doi.org/10.1021/np8003886
Abstract
Bredemolic acid (3) is a naturally occurring 2β,3α-isomer of maslinic acid (1) that is an allosteric site inhibitor of glycogen phosphorylase (GP). A practical synthesis of 3 was accomplished (18% yield) in five steps starting from the readily available 2β,3β-diol 6a. In a similar fashion, 2β,3α-dihydroxyurs-12-en-28-oic acid (4) was synthesized as a natural 2β,3α-isomer of corosolic acid (2). Compounds 3 and 4 exhibited significant inhibitory activity against rabbit muscle GPa with IC50 values of 6.25 and 1.1 μM, respectively.Keywords
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