4071-39-0

Usage

InChI:InChI=1/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7?,9?/m0/s1

Upstream product

• 102371-35-7 (1,2-bis-ethoxycarbonyl-4-isopropenyl-pyrrolidin-3-yl)-malonic acid diethyl ester 
• 87682-50-6 (+/-)-4c-isopropenyl-3t-methoxycarbonylmethyl-pyrrolidine-1,2r-dicarboxylic acid-1-ethyl ester-2-methyl ester 
• 108072-03-3 (2R,3S,4R)-1-Benzyl-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-2-carboxylic acid methyl ester 
• 98133-48-3 (+/-)-(2Ξ)-4c-((Ξ)-β-hydroxy-isopropyl)-3t-methoxycarbonylmethyl-pyrrolidine-1,2r-dicarboxylic acid-1-ethyl ester-2-methyl ester 
• 87682-50-6 (+/-)-4t-isopropenyl-3t-methoxycarbonylmethyl-pyrrolidine-1,2r-dicarboxylic acid-1-ethyl ester-2-methyl ester 
• 132286-62-5 ((2R,3R,4R)-1-Benzoyl-2-hydroxymethyl-4-isopropenyl-pyrrolidin-3-yl)-acetic acid methyl ester 
• 101020-91-1 (+/-)-[(3Ξ)-2t-carboxy-4c-((Ξ)-β-hydroxy-isopropyl)-pyrrolidin-3r-yl]-acetic acid 
• 100453-82-5 (+/-)-[(3Ξ)-4c-((Ξ)-β-ethoxy-isopropyl)-2t-carboxy-pyrrolidin-3r-yl]-acetic acid 
• 98133-48-3 (+/-)-(2Ξ)-4t-((Ξ)-β-hydroxy-isopropyl)-3t-methoxycarbonylmethyl-pyrrolidine-1,2r-dicarboxylic acid-1-ethyl ester-2-methyl ester 

Downstream Products

• 125292-93-5 [(3S)-2t-carboxy-4t-(α-hydroxy-isopropyl)-pyrrolidin-3r-yl]-acetic acid 
• 487-79-6 (-)-kainic acid 

Relevant academic research and scientific papers

Synthesis of (±)-β-Allokainic Acid

The total synthesis of kainoid alkaloid, (+/–)-β-allokainic acid is reported. The key step is a vinylogous Cloke–Wilson rearrangement followed by Lewis acid and transition metal induced transformations to prepare a highly functionalized pyrrolidine suitable for conversion to the target molecule.

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.

Substrate stereocontrol in the intramolecular organocatalyzed tsuji-trost reaction: Enantioselective synthesis of allokainates

Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.

Total synthesis of (±)-kainic acid: A photochemical C-H carbamoylation approach

A novel photochemical C-H carbamoylation of an octahydroisoindole derivative with PhNCO has allowed the authors to provide a unique access to a highly functionalized proline motif from which total synthesis of (±)-kainic acid, a bioactive marine alkaloid, has been accomplished.

Di- and trisubstituted γ-lactams via Rh(II)-carbenoid reaction of N -Cα-branched, N -Bis(trimethylsilyl)methyl α-diazoamides. Synthesis of (±)-α-allokainic acid

Acyclic N-Cα-branched, N-bis(trimethylsilyl)methyl (N-BTMSM) diazoamides undergo regio-, chemo-, and diastereoselective Rh(II)-carbenoid C-H insertion to give 4,5-disubstituted and 3,4,5-trisubstituted γ-lactams. The conformational influence of

Ruthenium-catalyzed cycloisomerizations of diynols

A wide variety of diynols containing tertiary, secondary, and primary propargylic alcohols undergo a cycloisomerization reaction to form dienones and dienals in the presence of a catalytic amount of [CpRu(CH3CN) 3]PF6. The

Stereocontrolled syntheses of kainoid amino acids from 7-azabicyclo[2.2.1] heptadienes using tandem radical addition-homoallylic radical rearrangement

N-Boc syn-7-(2-hydroxyethyl)-4-(alkyl or aryl)sulfonyl-2-azabicyclo[2.2.1] hept-5-enes serve as precursors in syntheses of the neuroexcitants 3-(carboxymethyl)pyrrolidine-2,4-dicarboxylic acid 43, α-kainic acid 12, α-isokainic acid 14, and α-dihydroalloka

Total synthesis of (+/-)-kainic Acid with an aza-[2,3]-Wittig sigmatropic rearrangement as the key stereochemical determining step.

A flexible route to the kainoid skeleton is exemplified by the synthesis of (+/-)-kainic acid from 3-butyn-1-ol. The route relies on the aza-[2,3]-Wittig sigmatropic rearrangement to efficiently install the relative stereochemistry between C2-C3. The C4 s

Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

N-Benzyl p-anisamide 6, on lithiation with Bu(t)Li in the presence of HMPA, undergoes a stereoselective anionic cyclisation with loss of aromaticity to give a bicyclic enone which may be converted in nine steps to (±)-kainic acid.

Stereoselective synthesis of (±)-α-kainic acid using free radical key reactions

Thiol-mediated free radical isomerization of a deliberately substituted but-3-enyl isocyanide 12a, and n-Bu3SnH/AIBN-mediated free radical cyclization of a deliberately substituted but-3-enyl isothiocyanate 22, afforded, respectively, the (ethylthio)pyrroline 13a and the thiopyroglutamates 5 and 23. Reduction, protection, and deprotection of these heterocyclic compounds afforded proline derivatives 6 and 25 which contain all the structural elements of α-kainic acid (1) except the C-2 acetic acid moiety. These intermediates were stereospecifically converted into (±)-α-kainic acid using a new method of temporary sulfur connection. Accordingly, CH2CO2Me is linked to the chiral isopropenyl anchor and then intramolecularly connected to the pyrrolidine ring and eventually disconnected from its anchor by a sequential reductive double elimination process in which the isopropenyl double bond is restored.