(+)-Aignopsanoic acid A, a sesquiterpene recently isolated from the sponge Cacospongia mycofijiensis, has been synthesized for the first time.
(+)-Microcionin-1, a structurally related furanosesquiterpene, was also prepared and could be converted via a simple oxidation process to (+)-aignopsanoic acid A. This transformation supports the hypothesis that (+)-microcionin-1 is an intermediate in the biosynthesis of aignopsanes.
This work was carried out in the group of Prof. Philippe Renaud.
C. Bürki, J. Bonjoch, B. Bradshaw, G. Villa, P. Renaud;
"Total Synthesis of Aignopsanes, A Class of Sesquiterpenes: (+)-Aignopsanoic Acid A, (-)-Methyl Aignopsanoate A, and (-)-Isoaignopsanoic A"
Chem. Eur. J., 21, 395-401, (2015);