Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates
Date
2008
Authors
Vernall, A.
Ballet, S.
Abell, A.
Editors
Advisors
Journal Title
Journal ISSN
Volume Title
Type:
Journal article
Citation
Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2008; 64(18):3980-3997
Statement of Responsibility
Andrea J. Vernall, Steven Ballet, Andrew D. Abell
Conference Name
Abstract
Olefin tethers of variable length, introduced into a natural amino acid (side-chain of Ser, Cys; N-terminus of Arg; C-terminus of Phe and Tic; and in both the side-chain and either the N- or C-terminus of Ser, Cys and Tyr), undergo metathesis on treatment with Grubbs' second generation catalyst. Side-chain linked dimers of Ser, Cys and Tyr were obtained by cross-metathesis, while olefin installation at the N- and C-terminus led to dimers of Arg and Phe (or Tic), respectively. Ring-closing metathesis of the doubly alkenylated derivatives of Ser, Cys and Tyr gave 12-, 20- and 24-membered macrocycles. © 2008 Elsevier Ltd. All rights reserved.