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 |
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Format: | Artikel |
Sprache: | eng |
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•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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2021.152912 |