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Short Paper | Special issue | Vol 97, No. 2, 2018, pp.1191-1202
Published online, 28th March, 2018
DOI: 10.3987/COM-18-S(T)66
Highly Convergent Straightforward Stereoselective Synthesis of (+)-C(9a)-Epiepiquinamide

Meriem Benlahrech, Alejandro Lahosa, Cherif Behloul,* Francisco Foubelo,* and Miguel Yus*

*Departamento de Química Orgánica, Universidad de Alicante, APDO 99-03080 Alicante, Spain

Abstract

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