A Versatile Method for the Preparation of Enantiomeric Benzene-1,2-bis(alanine) Derivatives

Abstract

A versatile method for the preparation of dicarba analogues of cystine as substituted benzene-, dihydrobenzene-, and tetrahydrobenzene-1,2-bis(alanine) derivatives is described. The partially saturated products resulted from Diels-Alder adduct formation with stereoselectively prepared (2R,7R)-2,7-diacetamido-4,5-bis (methylene)octane-1,8-dioic acid dimethyl ester. Aromatization of the dihydro adducts by manganese dioxide provided the parent benzene-1,2-bis(alanine) derivatives.

Keywords:

• Dicarba cystines
• Rigid bis(α-amino acids)
• Benzene-1,2-bis(alanines)