Degree Type

Dissertation

Date of Award

1988

Degree Name

Doctor of Philosophy

Department

Chemistry

First Advisor

George A. Kraus

Abstract

Nogalamycin is an anthracycline antibiotic that exhibits inhibitory activity against both gram-positive microorganisms and several types of cancer. Several analogs have been tested and were found to be more active than the parent compound. 7-Con-O-methylnogarol was one of the most active analogs;Research was undertaken to develop an enantiospecific synthesis of 7-con-O-methylnogarol and other analogs. The investigation involved: (1) preparation of a ketosugar with three contiguous stereogenic centers from D-arabinose; (2) synthesis of a tetracyclic moiety which could be transformed into ABCD ring system of the synthetic target; and (3) a stereoselective coupling reaction between the ketosugar and the tetracyclic moiety.

DOI

https://doi.org/10.31274/rtd-180813-9312

Publisher

Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/

Copyright Owner

Tim On Man

Language

en

Proquest ID

AAI8825417

File Format

application/pdf

File Size

103 pages

Share

COinS