Formal Synthesis of (±)-Methyl Rocaglate Using an Unprecedented Acetyl Bromide Mediated Nazarov Reaction

Abstract

To date the prototype Nazarov cyclization of a cross-conjugated pentadienone to the core structure of the rocaglate natural products has not been successful (9 into 12). It has been found that this conversion can be achieved by the use of acetylbromide in excellent yield and results in a strategically very direct route to these antitumor agents.