Synthetic studies toward the aziridinomitosene of FK317

ORGN 425

Susan Deeter, deetersu@umich.edu, Musong Kim, and Edwin Vedejs. Department of Chemistry, University of Michigan, 930 N. Univeristy, Ann Arbor, MI 48109
A synthetic approach to 1a, proposed by Fukuyama to be the active form of FR900482, and 1b, the proposed active form of semi-synthetic derivative FK317, will be described. A key step is the early installation of the labile aziridine through coupling of 2 and 3. Subsequent tin-lithium exchange and intramolecular Michael addition provides tetracycle 4. The difficult removal of the N-trityl group is accomplished without loss of the labile aziridine functionality to provide advanced intermediate 5. Studies toward the completion of the synthesis will be discussed.