A concise enantioselective synthesis of (R)-(+)-goniothalamin oxide, a trypanocidal active agent via L-prolinol catalyzed asymmetric epoxidation of cinnamaldehyde

Abstract

A short and straight-forward enantioselective synthesis of (<em>R</em>)-(+)-goniothalamin oxide <strong>2</strong> has been achieved with an overall yield of 39% and 99%<em> ee</em>. The synthetic approach involves l-prolinol catalyzed asymmetric epoxidation of cinnamaldehyde followed by Lewis acid-mediated diastereoselective allylation of epoxy aldehyde as the key chiral-inducing steps.