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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 24
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Original Articles

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

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Pages 4209-4220 | Received 04 Jul 2003, Published online: 21 Aug 2006
 

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.

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