Model studies in the lepadin series: synthesis of enantiopure decahydroquinolines by aminocyclization of 2-(3-aminoalkyl)cyclohexenones

Syntheses of enantiopure 3-acetoxy-2-methyldecahydroquinolines are accomplished by coupling cyclohexenyllithium with α-amino epoxides and an aminocyclization of 2-(3-aminoalkyl)cyclohexenones (i.e., and ) as the key steps. The procedure allows the incorporation of alkyl substituents at C(5) to give enantiopure 2,3,5-trisubstitued decahydroquinolines.