AI Article Synopsis
- A total synthesis of the AMPA/KA receptor antagonist (-)-kaitocephalin and its three diastereomers has been achieved.
- The process utilized substrate-controlled methods to synthesize alpha-formylglutamate, starting with alpha-hydroxymethylglutamate.
- Key stereocenters were created through selective reactions, including dihydroxylation, azide substitution, and copper-mediated allylation, followed by a simultaneous removal of protecting groups to yield the final product.
Article Abstract
[reaction: see text] Total synthesis of the potent AMPA/KA receptor antagonist (-)-kaitocephalin (1) and its three diastereomers has been accomplished. The synthesis features strictly substrate-controlled operations to alpha-formylglutamate 3 starting with alpha-hydroxymethylglutamate 4. The requisite 2R,3S,7R-stereocenters were efficiently constructed by manipulation of stereoselective reactions: dihydroxylation of 7 followed by azide substitution of the corresponding thionocarbonate 10 and Cu-mediated allylation of an acyliminium ion 21. All of the protecting groups in 26 were removed simultaneously by AlCl3/Me2S to give 1.
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