Synthetic studies of the macrolide structure of phorboxazole (C1-C26)

Patrick Bernard Greer, Marquette University


Phorboxazoles A and B are relatively new natural products from a new species of marine sponge called the Phorbas spongiastatin. Both compounds have shown exceedingly potent activity against a variety of human tumor cell lines. A recent round of testing by the National Cancer Institute's panel of 60 human tumor cell lines showed that phorboxazoles had growth inhibited (GI50 ) values that were lower than taxol in various cancer cells (lower the value-more potent the compound). The macrolide ring structure (C1-C26) was the target of interest. The retrosynthetic analysis used was similar to those reported in the literature. The retrosynthetic analysis in Scheme I shows two segments 1 and 2 . The goal was to use a two prong attack in creating good efficient, reproducible, and preparatory scale routes for each segment.* *Please refer to dissertation for diagrams.

Recommended Citation

Greer, Patrick Bernard, "Synthetic studies of the macrolide structure of phorboxazole (C1-C26)" (2000). Dissertations (1962 - 2010) Access via Proquest Digital Dissertations. AAI9977716.