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Chemistry of Natural Compounds

, Volume 50, Issue 6, pp 1071–1074 | Cite as

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

  • Mustafa Er
  • Necdet Coskun
Article
  • 136 Downloads

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.

Keywords

(±)-epi-cytoxazone 4-methoxyphenylglycidate Zn–TMSCl reduction Darzen epoxidation azides 

Notes

Acknowledgment

The Uludap University Research Fund is gratefully acknowledged for its financial support (Project No 2001-2).

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Mus Alparslan University, Department of ChemistryMusTurkey
  2. 2.Uludag University, Department of ChemistryBursaTurkey

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