Development of a Catalytic Asymmetric Synthesis of (+)-Alline Using Oxidative Proton-Coupled Electron Transfer

Abstract

Cyclotryptamine alkaloids have been targets of interest in synthetic chemistry for decades. In this thesis, I present a two-step catalytic asymmetric synthesis of (+)-alline from a TEMPO-trapped enantioenriched pyrroloindoline. Combined with the work by Knowles, a four-step synthesis of (+)-alline from commercially available tryptamine has been developed.18 Oxidative PCET was used to create the enantioenriched product, which then underwent a two-step reduction to achieve (+)-alline. It is hypothesized that alline can be activated with acid, and used as a building block to synthesize the oligomeric products, allowing for the synthesis of a variety of cyclotryptamine alkaloids.