Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates

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• 作者：Andrea J. Vernall ; Steven Ballet ; Andrew D. Abell
• 关键词：Cross-metathesis (CM) ; Ring-closing metathesis (RCM) ; Amino acid dimerization ; Cyclic amino acids
• 刊名：Tetrahedron
• 出版年：2008
• 出版时间：28 April 2008
• 年：2008
• 卷：64
• 期：18
• 页码：3980-3997
• 全文大小：1107 K

文摘

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.