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

Er, Mustafa; Coskun, Necdet

doi:10.1007/s10600-014-1161-z

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, Scopus)

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
Süleyman Demirel Üniversitesi Adresli: Hayır

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.