Date of Award
Doctor of Philosophy
During the last 10 years, adriamycin and daunomycin have been major components in the treatment of cancers. However, their toxicity has led to the search for less toxic anthracycline antibiotics. The 11-deoxyanthracyclines were discovered and have proven to be more effective anticancer drugs;A program was undertaken to develop a route to the linear tetracyclic ring system of the anthracyclines. This route was based on a sequential Diels-Alder/Friedel-Crafts strategy and has proven to be an effective approach for the expedient formation of anthracycline intermediates from a common starting material. These intermediates were successfully produced in 8 steps and possessed functionality for further elaboration to the deoxyanthracyclines;The sequential Diels-Alder/Friedel-Crafts strategy is also very versatile and should allow for the rapid formation of several novel anthracycline analogues.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Michael Don Hagen
Hagen, Michael Don, "Synthetic approaches to the deoxyanthracyclines " (1984). Retrospective Theses and Dissertations. 8168.