Molecule of the Month
October 2006
Total Synthesis of Lepadiformine

Lepadiformine is a marine alkaloid which was isolated in 1994 from the tunicate Clavelina lepadiformis and later from Clavelina moluccensis.
The total synthesis of lepadiformine has been achieved in 10 steps and 15% overall yield from cyclohexanone. The amino substituted quaternary carbon center is created through a radical carboazidation reaction.

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

References:

  • P. Schär, P. Renaud;
    "Total Synthesis of the Marine Alkaloid (±)-Lepadiformine via a Radical Carboazidation"
    Org. Lett., 8, 1569-1571, (2006); doi:10.1021/ol060083+.