An approach to a synthetic carboxylate-binding pocket based on β-avoparcin

Martin J. Stone, Martha S. Van Dyk, Paul M. Booth, Dudley H. Williams

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An approach to a macrocyclic lactam designed to bind to a carboxylate anion is described. The diaryl ether 8 was synthesised by Ullmann coupling of the protected 3-hydroxyphenylglycine derivative 7 and (E)-4-bromocinnamic acid methyl ester. Elaboration of an optically pure (R)-tyrosine synthon was achieved by transfer of electrophilic azide to the N-acyl oxazolidinone 12. The synthesis of a model system is also described.

Original languageEnglish
Pages (from-to)1629-1635
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number7
Publication statusPublished - 1991
Externally publishedYes

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