Please use this identifier to cite or link to this item:
http://arks.princeton.edu/ark:/88435/dsp01k3569761p
Title: | Exploration of Oxetane Formation via Swern Annulation on a Model System for the Synthesis of Curvularol |
Authors: | Park, Angela |
Advisors: | Sorensen, Erik J. |
Department: | Chemistry |
Class Year: | 2023 |
Abstract: | The Swern annulation is proposed as a new strategy to form highly substituted oxetanes on lactones. This approach is explored on a model system as part of efforts toward the total synthesis of curvularol, a structurally complex natural product with a rearranged trichothecene skeleton. Synthesizing the precursor of the Swern annulation via Giese addition was unproductive, which was hypothesized to be due to steric hindrance at the β-position of the disubstituted Michael Acceptor. These results directed subsequent efforts to synthesize a di- activated model system with an electron-withdrawing group at the α-position. While these endeavors faced challenges, promising avenues remain for synthesizing the di-activated model system. Lastly, the substrate scope of the Swern annulation was explored using a five-membered model system, whose photoinduced addition of isopropyl alcohol is known. With this photoadduct, oxetane formation via Swern annulation was observed. In closing, potential approaches for future study are proposed. |
URI: | http://arks.princeton.edu/ark:/88435/dsp01k3569761p |
Type of Material: | Princeton University Senior Theses |
Language: | en |
Appears in Collections: | Chemistry, 1926-2023 |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
PARK-ANGELA-THESIS.pdf | 1.32 MB | Adobe PDF | Request a copy |
Items in Dataspace are protected by copyright, with all rights reserved, unless otherwise indicated.