861145-05-3

Upstream product

• 440084-59-3 2-methylene-cyclopropanecarboxylic acid diphenyl amide 
• 929274-19-1 (R)-(-)-N-(4-methoxybenzylidene)-p-toluenesulfonamide 
• 861145-04-2 (2S,3S,S_R)-2-(4-methoxyphenyl)-4-methylene-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 

Downstream Products

• 861145-06-4 (2S,3S,4R,S_R)-4-formyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 
• 861145-08-6 (6S,3aR,6aS,S_R)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one 
• 861145-12-2 (2S,3S,4R,S_R)-[4-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde 
• 1027981-43-6 (2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid 
• 861145-13-3 (2S,3R,4S)-4-acetyl-3-methoxycarbonylmethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 861145-07-5 (2S,3S,4R,S_R)-4-(1-hydroxyethyl)-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 
• 487-79-6 (-)-kainic acid 
• 301832-55-3 (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid 
• 150674-69-4 methyl [2S-(2α,3β,4β)]-[2-(methoxycarbonyl)-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate 

Relevant academic research and scientific papers

Total synthesis of (-)-(α)-kainic acid via a diastereoselective methylenecyclopropane ring expansion

(Chemical Equation Presented) A concise and enantioselective synthesis of (-)-(α)-kainic acid in 13 steps with an overall yield of 15% is reported. The pyrrolidine kainoid precursor with the required C2/C3 trans stereochemistry was prepared with excellent diastereoselectivity (>20:1) via a Mgl 2-mediated ring expansion of a tertiary methylenecyclopropyl amide. A selective hydroboration was then employed to set the remaining stereochemistry at the C4 position en route to (-)-(α)-kainic acid.