Date Thesis Awarded
5-2022
Access Type
Honors Thesis -- Access Restricted On-Campus Only
Degree Name
Bachelors of Science (BS)
Department
Chemistry
Advisor
Jonathan Scheerer
Committee Members
Chris Abelt
Adrian Bravo
Abstract
The first study investigates a two-step sequence for synthesizing pyrrolodiketopiperazines beginning with an intact diketopiperazine ring and attaching a protected b-ketoaldehyde or alkynyl aldehyde in a mild aldol condensation, followed by pyrrole annulation using CSA or cationic gold complexes. The second study investigates a non-oxidative sequence for synthesizing 1,2-diketones beginning with a phosphonate ester linchpin molecule and extending outward using enolate-based bond constructions and nucleophilic addition of organometallic reagents. This method was successful in creating a diverse set of non-symmetric 1,2-diketones containing both alkyl and aryl side chains.
Recommended Citation
Pudner, Gwyneth, "I. Synthesis of Pyrrolodiketopiperazines from an Intact Diketopiperazine Ring II. A Non-oxidative Method for Synthesizing 1,2-diketones from Aldehyde and Organometallic Building Blocks" (2022). Undergraduate Honors Theses. William & Mary. Paper 1797.
https://scholarworks.wm.edu/honorstheses/1797
