Highly Convergent Straightforward Stereoselective Synthesis of (+)-C(9a)-epiepiquinamide

The total synthesis of (+)-C(9a)-epiepiquinamide has been achieved starting from ethyl 5-bromopentanoate, (Rs)-tert-butanesulfinamide, nitromethane, ethyl acrylate and acetic anhydride. The diastereoselective coupling of ethyl 4-nitrobutanoate and a chiral N-tert-butanesulfinyl imine, along with a double cyclization involving a primary amine through an intramolecular N-alkylation and lactam formation, are key steps of this synthesis.