Synthesis and biological activity of novel epothilone aziridines.

  title={Synthesis and biological activity of novel epothilone aziridines.},
  author={Alicia Regueiro-Ren and Robert M. Borzilleri and Xiao-jian Zheng and Sung Sun Kim and Joshua A. Johnson and Craig R. Fairchild and Francis Y. F. Lee and Byron Long and Gregory D. Vite},
  journal={Organic letters},
  volume={3 17},
[reaction: see text]. A series of 12alpha,13alpha-aziridinyl epothilone derivatives were synthesized in an efficient manner from epothilone A. The final semisynthetic route involves a formal double-inversion of stereochemistry at both the C12 and C13 positions. All aziridine analogues were tested for effects on tubulin binding polymerization and cytotoxicity. The results indicate that the aziridine moiety is a viable isosteric replacement for the epoxide in the case of epothilones.