Studies toward the synthesis of macrotermycin C: stereoselective construction of the acyclic skeleton of the aglycon.

The stereoselective construction of the acyclic skeleton of the aglycon of polyene macrolactam macrotermycin C has been achieved for the first time using a convergent strategy. The important features of this synthesis study include Evans methylation, Takai olefination, Sonogashira coupling followed by selective alkyne reduction, intermolecular Heck coupling, and Wittig olefination. Intramolecular Heck coupling has been tested for macrocyclization.