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

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