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Stereoselective synthesis of conformationally restricted analogues of aspartic and glutamic acids from endocyclic enecarbamates

✍ Scribed by Marcos JoséS. Carpes; Paulo Cesar M.L. Miranda; Carlos Roque D. Correia

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 263 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00238-4

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✦ Synopsis

The stereoselective synthesis of cyclic amino acids incorporating the core framework of aspartic acid and glutamic acids were accomplished from a common intermediate. Oxidative cleavage of an aza-bicyelio.dichlorocycldmtanone/pentanone with MeaCuLi/AcaO followed by ozonolysis furnished the amino acid derivatives in good overall yields in a three-step sequence. This protocol was also applied to the synthesis ofa c/s-~-amino acid and to the enantioselective construction of a chimeric amino acid incoq~orating the basic skeleton of four different naturally occurring amino acids into a single structure.

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