Date Thesis Awarded

4-2016

Access Type

Honors Thesis -- Access Restricted On-Campus Only

Degree Name

Bachelors of Science (BS)

Department

Chemistry

Advisor

Jonathan R. Scheerer

Committee Members

Robert J. Hinkle

John C. Poutsma

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.

Recommended Citation

Robins, Jacob Gabriel, "Construction of Bicyclo[2.2.2]diazaoctane Alkaloids via Intermolecular [4+2] Cycloadditions" (2016). Undergraduate Honors Theses. William & Mary. Paper 983.
https://scholarworks.wm.edu/honorstheses/983