The Total Synthesis of Roquefortine C and a Rationale for the Thermodynamic Stability of Isoroquefortine C over Roquefortine C

Abstract

The first total synthesis of roquefortine C is achieved by implementation of a novel elimination strategy to construct the thermodynamically unstable E-dehydrohistidine moiety. Molecular modeling studies are presented which explain the instability of the roquefortine C structure compared to that of isoroquefortine C.