Redefining the Synthetic Logic of Medicinal Chemistry. Photoredox-Catalyzed Reactions as a General Tool for Aliphatic Core Functionalization

David F. Fernández; María González-Esguevillas; Sebastian Keess; Felix Schäfer; Jens Mohr; Andre Shavnya; Thomas Knauber; David C. Blakemore; David W.C. MacMillan

doi:10.1021/acs.orglett.3c00994

Redefining the Synthetic Logic of Medicinal Chemistry. Photoredox-Catalyzed Reactions as a General Tool for Aliphatic Core Functionalization

David F. Fernández, María González-Esguevillas, Sebastian Keess, Felix Schäfer, Jens Mohr, Andre Shavnya, Thomas Knauber, David C. Blakemore, David W.C. MacMillan

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

C(sp³)-rich aliphatic motifs in drug molecules are strongly associated with clinical success. Historically, the availability of compound libraries based on C(sp³)-rich cores has been limited due to the challenging direct functionalization of aliphatic rings. Instead, most small molecule drug-like libraries are diversified around central aromatic rings. Herein, we present a general approach to the synthesis of diversified libraries featuring aliphatic core rings via photoredox catalysis under mild conditions.

Original language	English (US)
Pages (from-to)	2702-2707
Number of pages	6
Journal	Organic letters
Volume	26
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.3c00994
State	Published - Apr 12 2024

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c00994

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Fernández, D. F., González-Esguevillas, M., Keess, S., Schäfer, F., Mohr, J., Shavnya, A., Knauber, T., Blakemore, D. C., & MacMillan, D. W. C. (2024). Redefining the Synthetic Logic of Medicinal Chemistry. Photoredox-Catalyzed Reactions as a General Tool for Aliphatic Core Functionalization. Organic letters, 26(14), 2702-2707. https://doi.org/10.1021/acs.orglett.3c00994

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abstract = "C(sp3)-rich aliphatic motifs in drug molecules are strongly associated with clinical success. Historically, the availability of compound libraries based on C(sp3)-rich cores has been limited due to the challenging direct functionalization of aliphatic rings. Instead, most small molecule drug-like libraries are diversified around central aromatic rings. Herein, we present a general approach to the synthesis of diversified libraries featuring aliphatic core rings via photoredox catalysis under mild conditions.",

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Fernández, DF, González-Esguevillas, M, Keess, S, Schäfer, F, Mohr, J, Shavnya, A, Knauber, T, Blakemore, DC & MacMillan, DWC 2024, 'Redefining the Synthetic Logic of Medicinal Chemistry. Photoredox-Catalyzed Reactions as a General Tool for Aliphatic Core Functionalization', Organic letters, vol. 26, no. 14, pp. 2702-2707. https://doi.org/10.1021/acs.orglett.3c00994

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AU - Fernández, David F.

AU - González-Esguevillas, María

AU - Keess, Sebastian

AU - Schäfer, Felix

AU - Mohr, Jens

AU - Shavnya, Andre

AU - Knauber, Thomas

AU - Blakemore, David C.

AU - MacMillan, David W.C.

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AB - C(sp3)-rich aliphatic motifs in drug molecules are strongly associated with clinical success. Historically, the availability of compound libraries based on C(sp3)-rich cores has been limited due to the challenging direct functionalization of aliphatic rings. Instead, most small molecule drug-like libraries are diversified around central aromatic rings. Herein, we present a general approach to the synthesis of diversified libraries featuring aliphatic core rings via photoredox catalysis under mild conditions.

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Redefining the Synthetic Logic of Medicinal Chemistry. Photoredox-Catalyzed Reactions as a General Tool for Aliphatic Core Functionalization

Abstract

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