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, cilt.50, sa.6, ss.1071-1074, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 50 Sayı: 6
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1007/s10600-014-1161-z
  • Dergi Adı: CHEMISTRY OF NATURAL COMPOUNDS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1071-1074
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

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.