First Stereoselective Total Synthesis of Tumonoic Acid A and its Derivatives

Abstract

Abstract An efficient protecting-group-free synthesis of tumonoic acid A and its derivatives has been accomplished. The synthesis started from commercially available n-octanal and employs the magnesium chloride catalysed anti-aldol reaction under the Evans protocol as the key step. Ethyl tumonoate A is a new tumonoic acid derivative with anti-inflammatory activity and inhibitory activity towards calcium oscillations in neocortical neurons.

Keywords

• n-octanal
• wittig reaction
• chiral auxiliary
• hydrolysis
• coupling