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Synfacts 2022; 18(07): 0818
DOI: 10.1055/s-0041-1737671
Peptide Chemistry

Synthesis of Functionalized and Macrocyclic Peptides by C–H Olefination

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Cai C, Wang F, Xiao X, Sheng W, Liu S, Chen J, Zheng J, Xie R, Bai Z, *, Wang H. * Nanjing University, P. R. of China
Macrocyclization of Bioactive Peptides with Internal Thiazole Motifs via Palladium-Catalyzed C–H Olefination.

Chem. Commun. 2022;
58: 4861-4864
DOI: 10.1039/D1CC06764H.
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Key words

palladium catalysis - macrocyclic peptides - thiazoles - C–H bond activation - olefination

Significance

C–H bond activation is one of the powerful tools in organic synthesis for building complex bioactive molecules and natural products. In this present study, authors developed a palladium-catalyzed site-specific C(sp2)–H olefination of internal thiazole-containing peptides to synthesize functionalized and macrocyclic peptides.


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Comment

The developed palladium-catalyzed C–H olefination at the C-terminal of peptides having phenylalanine, tryptophan, or tyrosine residues proceeds smoothly to produce a series of functionalized peptides in good yields. The intramolecular olefination could also be performed efficiently to deliver macrocyclic peptides in moderate to good yields.


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Publication History

Article published online:
15 June 2022

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