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Updated: Aug 25, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Ring-closing metathesis: development of a cyclisation-cleavage strategy for the solid-phase synthesis of cyclic
Jean-Dominique Moriggi1, Lynda J Brown, José L Castro
1School of Chemistry, University of Southampton, Highfield, Southampton, UK SO17 1BJ.
Abstract:
A series of novel 7-membered cyclic sulfonamides have been synthesised using a solid-phase cyclisation-cleavage RCM strategy. Model solution studies indicated the sulfonamides were suitable substrates for RCM using the Grubbs' catalyst 2. Starting from either 2-carboxyethyl polystyrene (21) or Merrifield resin, various seven-membered sulfonamides were prepared in good to excellent yields at low catalyst loadings (2.5-5 mol%) using a flexible spacer between the polymer and the substrate. In addition, a novel double-armed linker was shown to allow efficient RCM cleavage of sulfonamides with as little as 1 mol% of the ruthenium alkylidene complex 2.
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