Olivomycin A, other olivomycins and other antitumor antibiotics such as the chromomycins and the mithramycins are all classed as the aureolic acid group. The variation in structure of this class of antibiotics is a function of a trisaccharide linked as a glycoside to C2 and a disaccharide similarly linked to C6. We propose a convergent synthesis of the aglycone of olivomycin which will permit variation in the structure of the tricyclic aromatic portion of the molecule as well as that of the oxygenated side chain. Methods somewhat related to the aureolic acid synthesis will be applied to the pyranoquinone antibiotics, exemplified by kalafungin. Biological activities of this class include antifungal, antimycoplasmal and antiprotazoal effects. Thus, we propose stereoselective and convergent syntheses of this family, incorporating sugars as part of the framework. In addition we propose a synthesis of U-58431, similar to other pyranoquinones and having a novel oxabicyclooctane structure.
| Franck, R W; Kaila, N (1993) Synthesis of the C'D' disaccharide of aureolic acid. Carbohydr Res 239:71-83 |
