Novel synthesis of right segment of solanoeclepin A

Abstract

The highly strained tricyclo[5.2.1.0(1,6)]decene skeleton of solanoeclepin A was synthesized through two key C-C bond forming processes; thus, a Hg(TFA)2-mediated oxymercuration followed an intramolecular aldol reaction to B and a SmI2-mediated cyclization of C between an aldehyde and an unsaturated ester to form the cyclobutane D having a tricyclo[5.2.1.0(1,6)]dodecene.