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Synfacts 2007(6): 0663-0663  
DOI: 10.1055/s-2007-968531
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

On-Resin Olefin Metathesis

Contributor(s): Yasuhiro Uozumi, Hiroe Takenaka
V. R. Pattabiraman, J. L. Stymiest, D. J. Derksen, N. I. Martin, J. C. Vederas*
University of Alberta, Edmonton, Canada
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

Solid-phase synthesis of peptide macrocycles was achieved by using Grubbs’ ring closing metathesis (RCM) as key steps. Tetrapeptide 1, anchored on the Wang resin, was treated with the Grubbs’ 2nd generation metathesis catalyst to give olefin-bridged (C-CH=CH-C) peptide macrocycle 2. Macrocycles B-ring and C-ring were synthesized via similar solid-phase peptide synthesis (standard Fmoc method) followed by the on-resin RCM. After cleavage of the resin, an overall yield of 0.5% (for 25 coupling steps and 3 RCM steps) of the desired lantibiotic peptide bearing the A-, B-, and C-rings, and the acyclic peptide chain of 15 amino acid units was obtained.