A Short and Efficient Asymmetric Synthesis of (+/-)-epi-Cytoxazone from cis-(1R,2S,5R)-Menthyl 4-Methoxyphenylglycidates

Abstract

The racemic epi-cytoxazone was synthesized, starting from p-anisaldehyde, in five steps and 48% overall yield. An efficient synthesis of azido alcohols has been achieved by regioselective ring opening of glycidates using NaN3 in MeOH-H2O. The key step of the process is reductive cyclization of azide carbonates by Zn-TMSCl.