A short entry to 3a-(o-nitrophenyl) octahydroindol-4-ones employing ozonolysis and double reductive amination of 2-allyl-2-(o-nitrophenyl)-1, 3-cyclohexanedione (9) is described. The symmetric dione 9 is synthesized in a 50% overall yield from 1, 3-cyclohexanedione by means of o-nitroarylation followed by O-allylation and subsequent Claisen rearrangement. Configurational and conformational aspects of azabicyclic derivatives 1 (ak) are discussed.
