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Synthesis of Colibactin Pyrrolidono[3,4-d]pyridones via Regioselective C(sp3)–H Activation


Ilazi, Agron; Huang, Bin; de Almeida Campos, Valery; Gademann, Karl (2020). Synthesis of Colibactin Pyrrolidono[3,4-d]pyridones via Regioselective C(sp3)–H Activation. Organic Letters, 22(17):6858-6862.

Abstract

The synthesis of pyrrolidono[3,4-d]pyridones of relevance to putative genotoxic colibactin structures featuring a doubly conjugated 1,6-Michael acceptor system is reported. We investigated and implemented a highly selective Pd-catalyzed C(sp3)–H activation reaction as a key step and further functionalized the pyridone core. Evaluating the role of this structural unit of relevance to colibactin, we found that this structure displayed a high degree of stability toward both acidic conditions and nucleophiles.

Abstract

The synthesis of pyrrolidono[3,4-d]pyridones of relevance to putative genotoxic colibactin structures featuring a doubly conjugated 1,6-Michael acceptor system is reported. We investigated and implemented a highly selective Pd-catalyzed C(sp3)–H activation reaction as a key step and further functionalized the pyridone core. Evaluating the role of this structural unit of relevance to colibactin, we found that this structure displayed a high degree of stability toward both acidic conditions and nucleophiles.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry
Language:English
Date:4 September 2020
Deposited On:20 Jan 2021 13:11
Last Modified:21 Jan 2021 21:03
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Closed
Publisher DOI:https://doi.org/10.1021/acs.orglett.0c02385

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Content: Accepted Version
Filetype: PDF - Registered users only until 1 September 2021
Size: 442kB
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Embargo till: 2021-09-01