Date Thesis Awarded
12-2018
Access Type
Honors Thesis -- Access Restricted On-Campus Only
Degree Name
Bachelors of Science (BS)
Department
Chemistry
Advisor
Jonathan Scheerer
Committee Members
Elizabeth Harbron
Jordan Walk
Abstract
This thesis outlines investigations into utilizing an intermolecular Diels-Alder approach to access the bicyclo[2.2.2]diazaoctane motif in natural products. A stereodivergent synthesis of prenylated indole alkaloid scaffolds from a common diene precursor, and a revised synthetic strategy to (±)-brevianamide B was a result of improved understanding of regioselectivity and stereoselectivity of intermolecular [4+2] between pyrazinone-type dienes and fumarate and maleic anhydride type dienophiles. This observed selectivity was also exploited in the synthesis of (+) serantrypinone, as the key Diels-Alder reaction between a chiral-nonracemic diene and an isatin derived dienophile proceeded with endo preference and exclusive regioselectivity. Progress of downstream elaborations from the cycloadduct towards (+)-serantrypinone is also reported.
Recommended Citation
Wang, Xiye, "Construction of Bicyclo[2.2.2]diazaoctane Scaffolds via Intermolecular Diels-Alder: Synthesis of (±)-Brevianamide B and Progress Toward (+)-Serantrypinone" (2018). Undergraduate Honors Theses. William & Mary. Paper 1271.
https://scholarworks.wm.edu/honorstheses/1271
