Regiospecific Construction of Polyoxygenated 9,10-Anthraquinones. Total Synthesis of Islandicin and Digitopurpone

Abstract
Current interest3 in a practical synthesis of the antibiotic adriamycin4 1 prompts us to report some consequences of the photochemical5 versus the Friedel-Crafts6 approaches in the construction of unsymmetrical polyhydroxy-anthraquinones. These two complementary methods have now been exploited in the preparation of the natural coloring matters islandicin,7 2, and digitopurpone,8 3.