126891-27-8

Upstream product

• 169774-79-2 (2S,3S,4S)-N-benzoyl-2-methoxycarbonyl-3-methoxycarbonylmethyl-4-phenylpyrrolidine 
• 160882-76-8 (2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 1268493-32-8 (R)-2-oxo-1-phenyl-2-(piperidin-1-yl)-ethyl 2-diazo-2-phenylacetate 
• 1268493-46-4 (R)-2-oxo-1-phenyl-2-(piperidin-1-yl)-ethyl 2-phenylacetate 
• 1268493-51-1 (2S,3S,4S)-3-(cyanomethyl)-4-phenylpyrrolidine-2-carbonitrile 
• 1268493-41-9 (2S,3S,4S)-3-(cyanomethyl)-1-(2-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile 
• 1268493-40-8 (2S,3S,4S)-3-(hydroxymethyl)-1-(2-nitrophenylsulfonyl)-4-phenylpyrrolidine-2-carbonitrile 
• 1268493-39-5 ((2R,3R,4S)-2-methoxy-1-(2-nitrophenylsulfonyl)-4-phenylpyrrolidin-3-yl)methanol 

Relevant academic research and scientific papers

Synthesis of Kainoids and C4 Derivatives

A unified stereoselective synthesis of 4-substituted kainoids is reported. Four kainic acid analogues were obtained in 8-11 steps with up to 54% overall yields. Starting from trans-4-hydroxy-l-proline, the sequence enables a late-stage modification of C4 substituents with sp2 nucleophiles. Stereoselective steps include a cerium-promoted nucleophilic addition and a palladium-catalyzed reduction. A 10-step route to acid 21a was also established to enable ready functionalization of the C4 position.

Stereocontrolled synthesis of (+)-methoxyphenylkainic acid and (+)-phenylkainic acid

The efficient total syntheses of (+)-methoxyphenylkainic acid (3) and (+)-phenylkainic acid (4) were achieved using a rhodium carbenoid-mediated intermolecular C-H insertion reaction. Complete stereoselective construction of the kainoid skeleton was accom

Towards a versatile synthesis of kainoids II: Two methods for establishment of C-4 stereochemistry

Benzylic lactone hydrogenolysis and enamide reduction were used to generate protected C-4 aryl substituted kainoid analogues which were deprotected to their corresponding free amino acids. X-ray crystographic data were obtained for the C-4 2-MeOPh- analogue.

Synthesis of new acromelic acid congeners: Novel neuroexcitatory amino acids acting on glutamate receptor

A general synthetic method of acromelic acid congeners was developed. Various C4-substituents of this family was introduced by the substitution reaction of the corresponding tosylate with diaryl copper lithium. Phenyl derivative 11 showed comparable excitatory activity with kainic acid, and o-anisyl derivative 12 had most potent activity in this family.