Degree Type

Dissertation

Date of Award

1981

Degree Name

Doctor of Philosophy

Department

Chemistry

Abstract

Adriamycin and daunomycin are two important anticancer drugs. Their toxicity has led to the search for other anthracycline anticancer compounds. The 11-deoxyanthracyclines, especially aclacinomycin A, appear to be less toxic than adriamycin and daunomycin;A program to develop a total synthesis of the aglycone of aclacinomycin A, aklavinone, and its 4-deoxy analogue was undertaken. This work also led to an approach to the total synthesis of ekatetrone and its 4-deoxy analogue;The use of substituted phthalides in an annelation reaction allowed the rapid synthesis of tricyclic aromatic systems with functionality suitable for further elaboration to aklavinone and ekatetrone. A phthalide annelation initiated an efficient two step synthesis of pachybasin. Protected o-carboxymethyl cyanohydrins and an o-carboxyethyl thioacetal were also found to undergo annelation reactions.

DOI

https://doi.org/10.31274/rtd-180813-4653

Publisher

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

Copyright Owner

Steven Rodney Crowley

Language

en

Proquest ID

AAI8123122

File Format

application/pdf

File Size

109 pages

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