DOI: https://doi.org/10.55373/mjchem.v24i2.258

Keywords: Azide reduction; epoxide; epoxidation; ring opening; Tamiflu

Abstract

A new method for the synthesis of Tamiflu intermediate starting with meso mono-epoxide cyclohexene has been developed. The key synthon tert-butyl(5-hydroxy-6-(1-ethylpropoxy)-1,2-epoxycyclohex-3-en-1-yl)carbamate was synthesized initially by the asymmetric epoxide ring opening reaction using a salen complex catalyst followed by reduction of the azide, amine protection, allylic hydroxylation, alcoholysis with 3-pentanol and epoxidation.