Date of Award
Doctor of Philosophy
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.
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Steven Rodney Crowley
Crowley, Steven Rodney, "Studies in anthracycline synthesis " (1981). Retrospective Theses and Dissertations. 6877.