Molecule of the Month
September 2013
First Total Synthesis of Aignopsanoic Acid A

The aignopsanes, a new class of sesquiterpenes, have been isolated in 2009 from the Indo Pacific marine sponge Cacospongia mycofijiensis. A member of this family, aignopsanoic acid A, could be prepared in seven steps starting from the easily available Wieland-Miescher ketone.

This total synthesis has been carried out by CÚdric BŘrki in the group of Prof. Philippe Renaud in collaboration with the group of Prof. Josep Bonjoch (Universitat de Barcelona).

References:

  • T. A. Johnson, T. Amagata, K. V. Sashidhara, A. G. Oliver, K. Tenney, T. Matainaho, K. K.-H. Ang, J. H. McKerrow, P. Crews;
    "The Aignopsanes, a New Class of Sesquiterpenes from Selected Chemotypes of the Sponge Cacospongia mycofijiensis"
    Org. Lett., 11, 1975-1978, (2009); doi:10.1021/ol900446d.