Princeton University Library Catalog

Progress Toward the Incorporation of Photocatalytic PCET in the Syntheses of Zearalenone and Quinine

Author/​Artist:
Culbertson, Bruce [Browse]
Format:
Senior thesis
Language:
English
Advisor(s):
Sorensen, Erik J. [Browse]
Department:
Princeton University. Department of Chemistry [Browse]
Class year:
2017
Summary note:
Recent collaboration between the Knowles and Sorensen groups in the field of proton coupled electron transfer (PCET) has led to the development of a new oxidative dehydrogenation reaction that relies on iridium and cobalt catalysts to cleave a carbon-carbon bond and abstract two hydrogen atoms from tertiary alcohol substrates, resulting in novel, ring-opening transformations. I investigated the applicability of this reaction to the syntheses of two biologically active natural products: zearalenone and quinine. In the case of zearalenone, I examined one model system and showed that the new PCET reaction could be used to transform a fused, five- and six-membered bicycle into one nine-membered ring. In the case of quinine, I explored two model systems meant to test the compatibility of the two halves of the quinine molecule with the PCET reaction. I did not reach the key step in either of the quinine model systems, but I was able to provide results that will be of value in the actual synthesis.