Abstract Reaction of 1-methyl-3, 4-dihydro-β-carboline 1 with methyl glycidate 4 gave the novel tetracyclic conjugated γ-lactam, 2-methylpyrrolo [1′, 2′: 1, 2] pyrido [3, 4–6] indol-3- one 5. The same compound 5 was obtained in higher yield when 1 was treated with methyl 2-methoxyacrylate 7. Sodium borohydride treatment of 5 resulted in the cleavage of lactam to yield the unexpected alcohols 8 and 9.