Total Synthesis and Structure Revision of (+)-Lancilactone C.

ABSTRACT

Lancilactone C is a tricyclic triterpenoid that inhibits human immunodeficiency virus (HIV) replication in H9 lymphocytes with no cytotoxicity. Its tricyclic skeleton comprises trans-dimethylbicyclo[4.3.0]nonane and 7-isopropylenecyclohepta-1,3,5-triene. The latter unique structure, in which all carbon atoms are sp2 hybridized, is not found in other triterpenoids and needs to be verified synthetically. Herein, we have accomplished the first total synthesis of lancilactone C (proposed structure) by developing a new domino [4 + 3] cycloaddition reaction involving oxidation, Diels-Alder reaction, elimination, and electrocyclization. We have also revised the structure based on the total synthesis of lancilactone C according to its plausible biosynthetic pathway.