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

ER M., Coskun N.

CHEMISTRY OF NATURAL COMPOUNDS, vol.50, no.6, pp.1071-1074, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 50 Issue: 6
  • Publication Date: 2014
  • Doi Number: 10.1007/s10600-014-1161-z
  • Journal Name: CHEMISTRY OF NATURAL COMPOUNDS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1071-1074
  • Bursa Uludag University Affiliated: Yes

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.