Synthesis of tryptophan-containing 2,5-diketopiperazines via sequential C–H activation: total syntheses of tryprostatin A, maremycins A and B DOI Creative Commons

Xue‐Song Yin,

Weiyi Qi, Bing‐Feng Shi

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(39), P. 13137 - 13143

Published: Jan. 1, 2021

Indole 2,5-diketopiperazines (DKPs) are an important type of metabolic cyclic dipeptides containing a tryptophan (Trp) unit possessing range interesting biological activities. The intriguing structural features and divergent activities have stimulated tremendous efforts towards their efficient synthesis. Herein, we report the development unified strategy for synthesis three Trp-containing DKPs, namely tryprostatin A, maremycins A B, via sequential C-H activation strategy. key Trp skeletons were synthesized from inexpensive, readily available alanine Pd(ii)-catalyzed β-methyl C(sp3)-H monoarylation. subsequent C2-selective prenylation resulting 6-OMe-Trp by Pd/norbornene-promoted led to total in 12 linear steps with 25% overall yield. Meanwhile, syntheses B successfully accomplished using Pd-catalyzed methylene methylation as step 15 alanine.

Language: Английский

Methionine-Enabled Peptides Modification through Late-stage Pd-catalyzed β-C(sp3)-H olefination/cyclization DOI

Fengjie Lu,

Xinyi Zhang,

Yujie Geng

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(61), P. 7942 - 7945

Published: Jan. 1, 2024

We present a method for site-selective diversification of peptides via Pd-catalyzed β-C(sp 3 )–H olefination/cyclization.

Language: Английский

Citations

3
Late-Stage Glycosylation of Peptides by Methionine-Directed β-C(sp3)–H Functionalization with 1-Iodoglycals DOI

Yunhao Ding,

Bo Yao

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7128 - 7133

Published: Aug. 19, 2024

Using l-methionine (Met) as the endogenous directing group, we developed Pd-catalyzed β-C(sp3)–H glycosylation of peptides with 1-iodoglycals. A wide range tri- to hexapeptides containing Ala-Met motifs underwent Ala C–H under standard conditions give glycopeptides smoothly. 15 proteinogenic amino acids (with easily removable protecting groups) were well tolerated. Control experiments indicated that Met acted a N,S-bidentate group and exhibited an effect superior other acid residues such l-aspartic (Asp), l-asparagine (Asn), S-protected l-cysteine (Cys). In addition, further transformation by HFIP-promoted 1,4-elimination furnished another type glycopeptide 1,3-diene motif, which provides handle for derivatization.

Language: Английский

Citations

3
Post-synthetic Chemical Functionalization of Peptides DOI

Stephanie A. Barros,

Rosaura Padilla‐Salinas, Irini Abdiaj

et al.

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
Insights into the mechanism of 3d transition-metal-catalyzed directed C(sp3)–H bond functionalization reactions DOI Creative Commons

Andrés García‐Viada,

Juan C. Carretero, Javier Adrio

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review provides an overview of the research advaces in Ni-, Cu-, Fe- and Co-catalyzed directed C(sp 3 )–H bond functionalization reactions; including design principles, mechanistic discussions, along with potential applications limitations.

Language: Английский

Citations

0
Synthesis of tryptophan-containing 2,5-diketopiperazines via sequential C–H activation: total syntheses of tryprostatin A, maremycins A and B DOI Creative Commons

Xue‐Song Yin,

Weiyi Qi, Bing‐Feng Shi

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(39), P. 13137 - 13143

Published: Jan. 1, 2021

Indole 2,5-diketopiperazines (DKPs) are an important type of metabolic cyclic dipeptides containing a tryptophan (Trp) unit possessing range interesting biological activities. The intriguing structural features and divergent activities have stimulated tremendous efforts towards their efficient synthesis. Herein, we report the development unified strategy for synthesis three Trp-containing DKPs, namely tryprostatin A, maremycins A B, via sequential C-H activation strategy. key Trp skeletons were synthesized from inexpensive, readily available alanine Pd(ii)-catalyzed β-methyl C(sp3)-H monoarylation. subsequent C2-selective prenylation resulting 6-OMe-Trp by Pd/norbornene-promoted led to total in 12 linear steps with 25% overall yield. Meanwhile, syntheses B successfully accomplished using Pd-catalyzed methylene methylation as step 15 alanine.

Language: Английский

Citations

23