The objectives of this research program are to complete the synthesis of calicheamicinone and adapt it into an enantiospecific synthesis. It will be the shortest synthesis by at least ten steps. To synthesize isocalicheamicinone, an 2,3-aziridine analogue of calicheamicinone (prodrug) that cannot form a 1, 4-diyl until the aziridine ring is opened (rearranged). Further studies on the dynemicin core structure and completion of its synthesis will be undertaken. Synthesis of the kedarcidin enediyne core structure using the information learned from our work on the neocarzinostatin core will be studies. New synthetic methodology will be developed to assist in the above specific problems. All of the research targets have potential antitumor activity, and will be screened by Bristol-Myers Squibb. The information contained in this proposal is protected by a patient application by The University of Texas at Austin: For additional information contact Dr. Philip Magnus at (512) 471-3966.
| Magnus, Philip; Turnbull, Rachel (2006) Thermal and acid-catalyzed Hofmann-Martius rearrangement of 3-N-aryl-2-oxindoles into 3-(arylamino)-2-oxindoles. Org Lett 8:3497-9 |
| Goldberg, Frederick W; Magnus, Philip; Turnbull, Rachel (2005) A mild thermal and acid-catalyzed rearrangement of O-aryl ethers into ortho-hydroxy arenes. Org Lett 7:4531-4 |
