First synthesis of (+)-myrrhanol C, an anti-prostate cancer lead.

The first synthesis of (+)-myrrhanol C (1), an antitumor polypodane-type bicyclic triterpene with inhibitory activity against androgen insensitive prostate cancers, is reported herein (IC(50) 10 μmolar). A key step in our convergent synthesis of (+)-myrrhanol C and related analogues is the employment of a microbial stereo- and regioselective late stage C-H oxidation. A low-waste and sustainable process has been developed to prepare (+)-myrrhanol C for further biological studies.