120229-02-9

Upstream product

• 120229-01-8 (2R,3S,4S)-4-(1-Chloromethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 186581-53-3 diazomethane 
• 501-53-1 benzyl chloroformate 
• 391677-13-7 (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester 
• 120211-85-0 (2R,3S,4S)-4-(1-Formyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 120211-86-1 (2R,3S,4S)-4-(1-Hydroxymethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 542-92-7 cyclopenta-1,3-diene 
• 3426-71-9 Benzyl N-hydroxycarbamate 

Downstream Products

• 115890-53-4 1-(benzyloxycarbonyl)kainic acid dimethyl ester 
• 73903-33-0 (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid 

Relevant academic research and scientific papers

Intramolecular ene reaction on a bicyclo[3.2.1]octane system: An alternative route to (-)-kainic acid

The intramolecular ene reaction of the 1,6-diene on a bicyclo[3.2.1]octane framework proceeds in a highly diastereoselective manner to form a trisubstituted pyrrolidine on the pyran ring in excellent yield. Its stereochemistry has been determined unambiguously by converting it into the known compound serving as a key intermediate of (-)-kainic acid.

A concise route to (-)-kainic acid.

A concise route to (-)-kainic acid from enantiopure (+)-cis-4-carbobenzoxyamino-2-cyclopentenol has been devised by employing concurrent Chugaev syn-elimination and intramolecular ene reaction as the key step.

A Concise Enantioselective Route to (-)-Kainic acid from (S)-2-(Benzyloxymethyl)oxirane

A concise enantioselective route to (-)-kainic acid (1) from (S)-2-(benzyloxymethyl)oxirane (2) has been established by enentio- and diastereo-selective intramolecular 1,3-dipolar cyclization.