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SYNFACTS | SYNFACT of the Month 2020-05-20

Cyclic Peptides Synthesis with the Assistance of a Removable Activating Group

Contributors: Hisashi Yamamoto, An Wu

Ben-Lulu M, Gaster E, Libman A, Pappo D. * Ben-Gurion University of the Negev, Beer Sheva, Israel

Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions

Angew. Chem. Int. Ed. 2020;
DOI: 10.1002/anie.201913305.


Key Words

oxidative cross-coupling - cyclic peptides - biaryl-bridged peptides - activating group

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Significance

Biaryl-bridged cyclic peptides are becoming more and more important due to their biological activity. The authors have developed an efficient strategy to synthesize these peptides by introducing a removable activating group to increase reactivity in the oxidative cross-coupling step that forms the biaryl unit.


Comment

Although the authors have prepared some natural and nonnatural biaryl-bridged cyclic peptides in moderate total yields, this approach with a remarkable activating group (t-Bu) might have more synthetic uses.

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