Stereoisomers of 4-amino3-hydroxy-1-cyclohexanecarboxylic acid and 4-amino-3-oxo-1-cyclohexanecarboxylic acid as mimetics of a twisted cis-amide bond

Stereoselective synthesis of the title compounds was performed. The relativ e configuration of methyl t-4-(tert-butoxycarbonylamino)-c-3-hydroxy-r-1-cy clohexanecarboxylate and methyl trans-4-(tert-butoxycarbonylamino)-3-oxo-r- 1-cyclohexanecarboxylate was confirmed by X-ray diffraction methods. Analog ues of cyclolinopeptide A (CLA) containing these twisted cis-amide bond mim etics were then synthesised. (C) 2001 Elsevier Science Ltd. All rights rese rved.