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Issue 10, 2020
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Macrocyclization via C–H functionalization: a new paradigm in macrocycle synthesis

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Abstract

The growing emphasis on macrocycles in engaging difficult therapeutic targets such as protein–protein interactions and GPCRs via preferential adaptation of bioactive and cell penetrating conformations has provided impetus to the search for de novo macrocyclization strategies that are efficient, chemically robust and amenable to diversity creation. An emerging macrocyclization paradigm based on the C–H activation logic, of particular promise in the macrocyclization of complex peptides, has added a new dimension to this pursuit, enabling efficacious access to macrocycles of various sizes and topologies with high atom and step economy. Significant achievements in macrocyclization methodologies and their applications in the synthesis of bioactive natural products and drug-like molecules, employing strategic variations of C–H activation are captured in this review. It is expected that this timely account will foster interest in newer ways of macrocycle construction among practitioners of organic synthesis and chemical biology to advance the field.

Graphical abstract: Macrocyclization via C–H functionalization: a new paradigm in macrocycle synthesis

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Article information


Submitted
31 Dec 2019
Accepted
17 Feb 2020
First published
18 Feb 2020

Org. Biomol. Chem., 2020,18, 1851-1876
Article type
Review Article

Macrocyclization via C–H functionalization: a new paradigm in macrocycle synthesis

S. Sengupta and G. Mehta, Org. Biomol. Chem., 2020, 18, 1851
DOI: 10.1039/C9OB02765C

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