Date Thesis Awarded

12-2018

Access Type

Honors Thesis -- Open Access

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.

Share

COinS