Controlled Synthesis of (S,S)-2,7-Diaminosuberic Acid: A Method for Regioselective Construction of Dicarba Analogues of Multicystine-Containing Peptides

Authors Jomana Elaridi, Jim Patel, W. Roy Jackson and Andrea J. Robinson
Published Journal of Organic Chemistry
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Abstract

A method to facilitate regioselective formation of multiple dicarba isosteres of cystine is described. A sequence of ruthenium-catalyzed cross metathesis and rhodium-catalyzed hydrogenation of non-proteinaceous allylglycine derivatives has been developed to achieve high-yielding and unambiguous formation of diaminosuberic acid derivatives. Allylglycine derivatives readily undergo ruthenium-catalyzed metathesis and hydrogenation to yield diaminosuberic acid derivatives in near quantitative yield. Under the same experimental conditions, prenylglycine was found to be inert to both Grubbs’ and Wilkinson’s catalyzed metathesis and hydrogenation, respectively, but was readily activated for metathesis via cross metathesis with Z-butene. Subsequent cross metathesis of the metathesis-formed crotylglycine derivative, followed by hydrogenation, yielded the second diaminosuberic acid derivative in excellent yield.

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Citation J. Elaridi, J. Patel, W. R. Jackson, and A. J. Robinson, J. Org. Chem., 2006, 71, 7538-7545.
Doi DOI: 10.1021/jo0606913
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This entry was posted in Dicarba peptides, Metathesis, Publications, Publications pre 2009. Bookmark the permalink.

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