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  • Title: Practical synthesis of bredemolic acid, a natural inhibitor of glycogen phosphorylase.
    Author: Cheng K, Zhang P, Liu J, Xie J, Sun H.
    Journal: J Nat Prod; 2008 Nov; 71(11):1877-80. PubMed ID: 18847277.
    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 IC(50) values of 6.25 and 1.1 μM, respectively.
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