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Synfacts | Synfact of the Month 2023-09-01
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C–H Functionalization for the Synthesis of Maleimide-Decorated Peptides and Macrocyclic Peptides

Contributors:  Hisashi YamamotoIsai Ramakrishna

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Significance

Late-stage functionalization plays an inherent role in the construction of peptides and macrocyclic peptides. In the present study, the ­authors developed a Rh(III)-catalyzed alkenylation of tryptophan-containing peptides for the ­synthesis of maleimide-decorated peptides and macrocyclic peptides.

Comment

Rh(III)-catalyzed alkenylation of ­tryptophan-containing peptides proceeded smoothly to deliver maleimide-decorated peptides in good yields with excellent selectivity. The ­intramolecular reaction of maleimide-decorated peptides produced macrocyclic peptides.

Rh(III)-catalyzed alkenylation of ­tryptophan-containing peptides proceeded smoothly to deliver maleimide-decorated peptides in good yields with excellent selectivity. The ­intramolecular reaction of maleimide-decorated peptides produced macrocyclic peptides.

Macrocyclization of Maleimide-Decorated Peptides via Late-Stage Rh(III)-Catalyzed Trp(C7) Alkenylation

Org. Lett. 2023; 25: 2456-2460
DOI: 10.1021/acs.orglett.3c00601.