A short synthesis of both enantiomers of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid
2021
Charnay-Pouget, Florence | Le Liepvre, Matthieu | Eijsberg, Hendrik | Guillot, Régis | Ollivier, Jean | Secci, Francesco | Frongia, Angelo | Aitken, David J.
A concise method is reported for the synthesis of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid, a close analogue of the glutamate receptor ligand LY354740, in both enantiomeric forms. The strategy features the creation of the core structure at the start of the synthesis via a photochemical [2 + 2] cycloaddition reaction, an efficient resolution procedure using a chiral oxazolidinone, and requires only minimal purification of the synthetic intermediates. The title compounds showed little or no affinity for the mGlu2 and mGlu3 receptors.
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