Date Thesis Awarded

4-2016

Document Type

Honors Thesis

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Jonathan R. Scheerer

Committee Member

Robert J. Hinkle

Committee Member

John C. Poutsma

Committee Member

Diane C. Shakes

Abstract

The synthesis of bicyclo[2.2.2]diazaoctane prenylated indole alkaloids, containing both syn and anti ring fusion, is described. More than 100 examples of alkaloids in this family have been isolated and show a variety of potent bioactivities. This strategy utilizes the convergent and atom–economic intermolecular hetero Diels–Alder cycloaddition to construct the bicyclic nucleus from electron–deficient dienophiles and an electron–rich pyrazinone diene. The regiochemical and stereochemical implications of this cyclization are investigated.

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.

Available for download on Thursday, May 02, 2019

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