An approach to a synthetic carboxylate-binding pocket based on β-avoparcin
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1629-1635
- https://doi.org/10.1039/p19910001629
Abstract
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.Keywords
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