Dept. of Chemistry and Biochemical Sciences
Oregon Graduate Center
An expedient, regia- and stereospecific route for the construction of sugar analogs of 2, 6-epoxy-1(2H)-benzoxocins is described. The methodology involves the oxidation of furancarbinols followed by acidic hydrolysis to afford 2, 6-epoxy-1(2H)-ketobenzoxocin. Further functionalization affords sugar analogs with the manno, talo, altro and galacto configurations and aminosugar analogs with the ribo and arabino configurations. The preparation of benzoxocin DEF ring synthons to nogarol anthracyclines is also described. Oxidation of furancarbinols containing variously substituted benzene rings were converted to methyl hexenulose derivatives by acidic methanolysis. Functionalization of the hexenuloses afforded gluco configurated amino sugars. These highly functionalized gluco-2, 6-epoxy-1(2H)-benzoxocin analogues are suitable as synthons for the DEF ring system in nogarol anthracyclines.
Ellenberger, William Paul, "Synthesis of DEF ring synthons to nogarol anthracyclines" (1987). Scholar Archive. 233.