Phorbol

August 15, 2016
My complexity may be exceeded by my medical usefulness.
What molecule am I?

(+)-Phorbol is a long-known, structurally complex natural product. In 1934, Swiss chemists Bonifaz Flaschenträger and Rudolf von Wolffersdorff isolated it from hydrolyzed croton oil, which was a known tumor-promoting substance. Research teams led by E. Hecker in Germany and George Ferguson in Britain reported its structure in 1967.

According to the Merck Index, “Phorbol has a structural skeleton based on cyclopropabenzazulene.” It also has a daunting eight stereogenic centers. Three research groups have published total syntheses of phorbol, but the first two produced the racemic compound. Just this year, Phil S. Baran and colleagues at the Scripps Research Institute (La Jolla, CA) and LEO Pharma (Ballerup, Denmark) found a way to make phorbol enantioselectively in 19 steps, less than half the number required in earlier work.

Baran’s group’s work and future, more efficient syntheses should provide sufficient quantities of phorbol and its esters for potential drug development. In addition to their ability to promote rapid tumor growth, phorbol derivatives may be useful immunotherapy, antiviral, and anticancer drugs.

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