The condensation of phenyl hydrazine (I) with the cis N-methyl-perhydroisoindoletrione (II) gave hydrazone (III), which underwent Fischer indole synthesis upon treatment with methanolic H2SO4 to afford the pyrrolocarbazole (IV) as the major regioisomer (1). Reduction of the imide group of (IV) with aluminum hydride, generated from LiAlH4 and H2SO4, provided the corresponding amine as a racemic mixture. Separation of the desired (R,R)-enantiomer was then achieved by chiral HPLC on Chiralcel(R) OJ.