A new approach to asymmetric synthesis of (−)-epiquinamide from d-glucose

Abstract The asymmetric total synthesis of (−)-epiquinamide has been achieved starting from a 5-iodofuranoside synthon derived from d -glucose. The methods featured Bernet-Vasella reaction followed by Horner-Wadsworth-Emmons (HWE) reaction to provide a new chiral building block diene as the key steps. The bicyclic framework of this quinolizidine was constructed by selective reduction of α,β-unsaturated ester, intramolecular nucleophilic substitution and ring-closing metathesis.