Details

Autor(en) / Beteiligte

• Koch, Claus-Jürgen
• Höfner, G.
• Polborn, Kurt
• Wanner, Klaus Theodor

Titel

Synthesis of the Four Stereoisomers of 1-Amino-2-(hydroxymethyl)cyclobutanecarboxylic Acid and Their Biological Evaluation as Ligands for the Glycine Binding Site of the NMDA Receptor

Ist Teil von

• European journal of organic chemistry, 2003-06, Vol.2003 (12), p.2233-2242

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2003

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A synthesis of all four stereoisomers [(1S,2S)‐, (1R,2R)‐, (1S,2R)‐, (1R,2S)‐] of 1‐amino‐2‐(hydroxymethyl)cyclobutanecarboxyclic acid is presented. The synthesis is based on the chiral glycine equivalent 1, employed in both enantiomeric forms. The key step involves the cyclization of the silyl‐protected iodohydrins 5a−d to the corresponding spiro derivatives 6a−d with the aid of the phosphazenic base tBu‐P4. The final compounds were found to display moderate potency as ligands for the glycine binding site of the NMDA receptor. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)