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Title: Development of a Catalytic Asymmetric Synthesis of (+)-Alline Using Oxidative Proton-Coupled Electron Transfer
Authors: Matsuura, Rei
Advisors: Knowles, Robert R.
Department: Chemistry
Class Year: 2016
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.
Extent: 40 pages
Type of Material: Princeton University Senior Theses
Language: en_US
Appears in Collections:Chemistry, 1926-2017

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