Meayamycin B is the most potent inhibitor of bacterial natural product FR901464, which has a potent antitumor activity in a panel of cancer cell lines. Since its discovery, the natural product has garnered a lot of interest from both synthetic chemists and biologists. It is known to inhibit pre-mRNA splicing by modulating the splicing factor 3b complex and hence used as a chemical probe in splicing studies. Currently, there is an indirect route to meayamycin B, requiring extra steps to functionalize advanced intermediates in the existing scheme to the parent natural product FR901464. Our first generation synthesis of meayamycin B consisted of 30 total steps, many of which required toxic, hazardous, or expensive reagents. This prompted us to design a new synthesis of this compound. In this work we will report a more concise and greener synthesis of meayamycin B.

Second generation synthesis of meayamycin B

248th National Meeting (2014)

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