Herein we report a series of telescoping methodologies for one pot synthesis of biologically relevant γ-carboline derivatives 6 and spiro[pyrrolidinone-3,3']indole 7. Initially the three consecutive steps of cyclopropanation, phthalimide deprotection, and Boc-deprotection have been congregated in a single reaction vessel to afford a ∼1:1 mixture of 6 and 7. Next, careful optimization of the reaction sequence and the conditions generated an orthogonal approach to access compounds 6 and 7 exclusively. Air oxidation of the γ-carbolinones 6 afforded aromatic γ-carbolines 8.