Date of Award
Summer 2000
Document Type
Dissertation - Restricted
Degree Name
Doctor of Philosophy (PhD)
Department
Chemistry
First Advisor
Donaldson, William A.
Second Advisor
Haworth, Daniel T.
Third Advisor
Wilkie, Charles A.
Abstract
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 (GI 50 ) 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