Biomimetic Total Synthesis of (±)-Homodimericin A

Abstract

A biomimetic total synthesis of racemic homodimericin A was achieved in seven steps, including two cascade reactions. Aqueous buffer solutions are found to help both the oxidative dimerization cascade and the intramolecular Diels-Alder cascade. This synthetic sequence validates key steps in the biogenetic proposal of homodimericin A.

Keywords: Negishi coupling; biomimetic synthesis; cascade reactions; homodimericin; total synthesis.