Date Thesis Awarded
12-2018
Document Type
Honors Thesis
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. Paper 1271.
https://scholarworks.wm.edu/honorstheses/1271
