Molecule of the Month
October 2012
Diastereoselective Synthesis of a Mitomycin Derivative

Mitomycin alkaloids are an important class of bioactive natural products having potent antibiotic and antitumor properties.
By an efficient diastereoselective radical cascade/lactamisation sequence, a mitomycin derivative has been prepared from a highly functionalised ortho-azidoallylbenzene intermediate using triethylborane to initiate and sustain the radical step.

This work was carried out in the group of Prof. Philippe Renaud.


  • F. Brucelle, P. Renaud;
    "Synthesis of a Leucomitosane via a Diastereoselective Radical Cascade"
    J. Org. Chem., 78, 6245-6252, (2013); doi:10.1021/jo4009904.
  • F. Brucelle, P. Renaud;
    "Synthesis of Indolines, Indoles, and Benzopyrrolizidinones from Simple Aryl Azides"
    Org. Lett., 14, 3048-3051, (2012); doi:10.1021/ol301120w.