Pictet–Spengler synthesis of tetrahydro-β-carbolines using vinylsulfonylmethyl resin

Abstract A novel, solid phase Pictet–Spengler synthesis has been developed using vinylsulfonylmethyl resin. A library of 800 structurally diverse tetrahydro-β-carbolines was prepared in a four-step sequence starting from tryptamines. The final resin cleavage step enabled the introduction of a basic tertiary amine in the six-membered heterocyclic ring.