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Synfacts 2019; 15(09): 1071
DOI: 10.1055/s-0039-1690511
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Synthesis of Cyclophane-Braced Peptide Macrocycles

Contributor(s):
Hisashi Yamamoto
,
Manthena Chaithanya
Li B, Li X, Han B, Chen Z, Zhang X, He G, Chen G. * Nankai University, Tianjin, P. R. of China
Construction of Natural-Product-Like Cyclophane-Braced Peptide Macrocycles via sp3 C–H Arylation.

J. Am. Chem. Soc. 2019;
141: 9401-9407
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Further Information

Publication History

Publication Date:
20 August 2019 (online)

 
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Key words

palladium catalysis - cyclophanes - peptide macrocycles - arylation - picolinamides - directing groups

Significance

Cyclic peptides possess great ­potential for modulating challenging biological ­processes. The authors have developed a general method for the synthesis of cyclophane-braced peptide macrocycles through palladium-catalyzed C(sp3)–H arylation.


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Comment

Cyclophane motifs with unusual structural and stereochemical complexity were obtained by the picolinamide-directed intramolecular γ-selective C(sp3)–H arylation of the N-termini of peptide substrates at both the methyl and methylene positions.


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