A short synthesis of both enantiomers of 2-aminobicyclo[3.2.0]heptane-2,7-dicarboxylic acid

[Display omitted] •Photochemical access to a functionalized bicyclo[3.2.0]heptane skeleton.•Preparation of a constrained analogue of glutamic acid.•Use of an oxazolidinone for chiral resolution of an amino acid.•High stereoselectivity in a Bucherer-Bergs reaction. A concise method is reported for th...

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Veröffentlicht in:Tetrahedron letters 2021-03, Vol.68, p.152912, Article 152912
Hauptverfasser: Charnay-Pouget, Florence, Le Liepvre, Matthieu, Eijsberg, Hendrik, Guillot, Régis, Ollivier, Jean, Secci, Francesco, Frongia, Angelo, Aitken, David J.
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Sprache:eng
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Zusammenfassung:[Display omitted] •Photochemical access to a functionalized bicyclo[3.2.0]heptane skeleton.•Preparation of a constrained analogue of glutamic acid.•Use of an oxazolidinone for chiral resolution of an amino acid.•High stereoselectivity in a Bucherer-Bergs reaction. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.152912