150674-68-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 158839-31-7 (3aS,3bS)-6-Methyl-3a,3b,4,7-tetrahydro-3H-2-oxa-7a-azacyclopentapentalene-1,5-dione 
• 1374759-95-1 ((3S,3aS,5R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-tosyl-1,2,3,3a,4,5-hexahydrocyclopenta[c]pyrrol-5-yl)(phenyl)methanone 
• 1374759-92-8 ((3S,3aS,6aS)-3-(((tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-tosyl-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl)(phenyl)methanone 
• 1374759-96-2 methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate 
• 1374759-91-7 methyl-2-((2S,3S,4R)-4-acetyl-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylpyrrolidin-3-yl)acetate 
• 150674-63-8 N-But-2-ynyl-N-((S)-1-methoxymethoxymethyl-allyl)-4-methyl-benzenesulfonamide 
• 158839-34-0 (1S,3aS,4S,6aS)-1-(Hydroxymethyl)-4-methyl-2-(toluene-4-sulfonyl)-hexahydrocyclopentapyrrol-5-one 
• 158839-36-2 (3S,3aS)-3-(Hydroxymethyl)-6-methyl-2-(toluene-4-sulfonyl)-2,3,3a,4-tetrahydro-1H-cyclopentapyrrol-5-one 
• 158839-32-8 (S)-3-(but-2-ynyl)-4-vinyloxazolidin-2-one 
• 1026379-71-4 (3S,3aS)-3-Hydroxymethyl-6-methyl-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one 
• 150674-64-9 (1S,3aS,4S,6aS)-1-(Methoxymethoxymethyl)-4-methyl-2-(toluene-4-sulfonyl)hexahydrocyclopentapyrrol-5-one 
• 150674-66-1 (2S,3R,4R)-4-Acetyl-3-<(methoxycarbonyl)methyl>-2-(methoxymethoxymethyl)-1-(toluene-4-sulfonyl)pyrrolidine 
• 150674-65-0 (3S,3aS,6aS)-5-<(Trimethylsilyl)oxy>-3-(methoxymethoxymethyl)-6-methyl-2-(toluene-4-sulfonyl)-1,2,3,3a,4,6a-hexahydrocyclopentapyrrole 

Downstream Products

• 150674-69-4 methyl [2S-(2α,3β,4β)]-[2-(methoxycarbonyl)-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate 
• 301832-55-3 (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid 
• 487-79-6 (-)-kainic acid 

Relevant academic research and scientific papers

Total synthesis of (-)-(α)-kainic acid via a diastereoselective intramolecular [3 + 2] cycloaddition reaction of an aryl cyclopropyl ketone with an alkyne

An enantioselective synthesis of (-)-(α)-kainic acid in 15 steps with an overall yield of 24% is reported. The pyrrolidine kainoid precursor with the required C2/C3 trans stereochemistry was prepared with complete diastereoselectivity via an unprecedented SmI2-catalyzed intramolecular [3 + 2] cycloaddition reaction of an aryl cyclopropyl ketone and an alkyne. Double bond isomerization was then employed to set the remaining stereochemistry at the C4 position en route to (-)-(α)-kainic acid.

Radical cyclization in heterocycle synthesis. Part 10: A concise synthesis of (-)-kainic acid via sulfanyl radical addition-cyclization-elimination reaction

Sulfanyl radical addition-cyclization-elimination of diallylamines in the presence of thiophenol and AIBN gave the 2,3,4-trisubstituted pyrrolidine in high yield. This reaction was extended to a radical cyclization using a catalytic amount of thiophenol. A successful application was demonstrated by the asymmetric synthesis of (-)-kainic acid. (C) 2000 Elsevier Science Ltd.

An Enantioselective Synthesis of (-)-α-Kainic Acid via Thiyl Radical Addition-Cyclization-Elimination Reaction

An enantioselective synthesis of (-)-α-kainic acid has been achieved via the route involving thiyl radical addition-cyclization-elimination reaction.

A Total Synthesis of (-)-α-Kainic Acid Involving a Pauson-Khand Reaction as the Key Step

A synthetic route to (-)-α-kainic acid has been developed based on the Pauson-Khand reaction as a key step for the construction of the bicyclic ring system.In this reaction a built-in oxazolidinone ring serves as a rigid template for good diastereofacial selectivity.

A Total Synthesis of (-)-α-Kainic Acid By the Pauson-Khand Reaction

A total synthetic route to (-)-α-kainic acid has been developed based on the Pauson-Khand reaction as a key reaction for the construction of the bicyclo ring system.