Related Experiment Video
Updated: May 29, 2025

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and
Asahi Kanno1, Ryo Tanifuji1, Satoshi Yoshida2
1Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Abstract:
The integration of copper(I)-catalyzed three-component coupling with gold(I)-mediated 6-endo cyclization streamlines the rapid and modular assembly of the substructure of bis-tetrahydroisoquinoline (THIQ) alkaloids. The design of the key synthetic intermediate bearing a 2,3-diaminobenzofuran moiety allows both gold(I)-mediated regiocontrolled 6-endo hydroamination and temporary protection of nitrile and phenolic hydroxy groups. The synthetic strategy enabled the efficient synthesis of the substructure of saframycins bearing isoquinoline and THIQ units in just four steps from the modular assembly of the three components. We also found the unexpected involvement of a fluorescent intermediate in the cascade synthetic process.
More Related Videos
Related Concept Videos
Cycloaddition Reactions: Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

