Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone

Abstract

Optically pure (-)-cytoxazone was synthesized, starting from methyl p-methoxycinnamate, in six steps and in 31%, overall yield. The required anti-aminoalcohol configuration was established by combining Sharpless asymmetric aminohydroxylation with the configurational inversion of the intermediate amidoalcohol via ail oxazoline. The synthesis of (+)-epi-cytoxazone is also described. (C) 2003 Elsevier Ltd. All rights reserved.