Dithiane-Alkyne Metathesis Enables Trp(C2)-Alkene-Cross-Linked Cyclic Peptides

Organic Letters 2026

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Authors: Liang Li, Xiaomeng Gong, Guohong Tang, Yingying Xue, Zhuzhu Zhang, Ruipeng Li, Shouchu Tang
DOI: 10.1021/acs.orglett.6c00101
Cited by: 1
References: 36

Abstract

Cyclic peptides represent a privileged class of scaffolds in drug discovery owing to their unique balance between structural rigidity and functional diversity. Herein, we disclose an indium(III)-catalyzed intramolecular dithiane-alkyne metathesis (DAM) that facilitates the efficient construction of Trp(C2)-alkene-cross-linked cyclic peptides with exclusive E -selectivity. This protocol directly transforms linear peptide precursors into diverse macrocycles with broad substrate scope, high atom economy, and operational simplicity. These features establish DAM as a mechanistically distinct and practical peptide stapling strategy.

Fields of Study & Subjects

Synthetic Organic Chemistry Methods Chemical Synthesis and Analysis Supramolecular Chemistry and Complexes

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
7
Pages
2437–2442
Publication date
10 February 2026
Language
EN