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
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.
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.
