Olivomycin A (1) is one member of the aureolic acid group of polysaccharide antitumor antibiotics. Certain members of the group, including aureolic acid (3), are used clinically for treatment of testicular tumors. We propose herein to develop a convergent, stereoselective synthesis of olivomycin A. The aglycone, olivin, and the di- and trisaccharide residues will be synthesized and then will be coupled at a final stage of the synthesis. Considerable progress towards olivin and the carbohydrate residues was realized in the first two years of this grant. These segments of the project will be completed in the coming grant period and then we will turn our full attention to the major problem posed by the coupling of the subunits. Methods for the synthesis of 2-deoxy-beta-glycosides will be explored and developed. The convergent strategy proposed may prove useful in syntheses of analogues with improved therapeutic indices.
| Roush, W R; Hagadorn, S M (1985) Synthesis of mycarose and epi-axenose from non-carbohydrate precursors. Carbohydr Res 136:187-93 |
