A diastereoselective synthesis of (-)-2-ethyloctahydroindol-6-one 12 starting from O-methyl-L-tyrosine 1 is described. The process first involves the synthesis of enantiopure (-)-1-(4-methoxyphenyl)-2-butylamine 8, which, after Birch reduction, N-benzylation and acid treatment, renders the cis-fused azabicyclo 12. Studies on the Fischer indolization of 12 are also reported. (C) 1997 Elsevier Science Ltd.