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

Abstract

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.