206126-48-9

Upstream product

• 206126-43-4 (2R,3S,4R)-3-(Bis-ethoxycarbonyl-methyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 206126-45-6 (2R,3R,4R)-3-(Bis-ethoxycarbonyl-methyl)-4-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 206126-40-1 (2S,4S)-4-(1-Hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 206126-44-5 (2R,4R)-3-(Bis-ethoxycarbonyl-methylene)-4-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 206126-46-7 (2R,3S,4R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-ethoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 206126-42-3 (R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 206126-41-2 (2S,4R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 1066877-98-2 (S)-4-(1-Hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 206126-47-8 (2R,3S,4R)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-3-ethoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester 

Downstream Products

• 206126-49-0 (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester 
• 487-79-6 (-)-kainic acid 
• 115890-53-4 1-(benzyloxycarbonyl)kainic acid dimethyl ester 

Relevant academic research and scientific papers

New enantioseleetive approach to the total synthesis of (-)-α-Kainic Acid

The total synthesis of (-)-α-Kainic Acid 1 has been accomplished using ethyl N-Boc-pyroglutamate 2 as starting material. The isopropenyl appendage was achieved from the elimination of the dimethylcarbinol introduced at C-4 via an aldol condensation of the lactam enolate of 2 and acetone. The acetate group at C-3 of the kainic acid structure was introduced via diethyl malonate Michael addition reaction to the 2,3-didehydroprolinate 8. This Michael addition reaction proceeds with complete stereocontrol over the newly generated stereogenic centres. Inversion of the configuration at C-3 in 9 through double bond formation followed by hydrogenation, neutral decarboxylation and further epimerization of the C-2 stereogenic centre in 12, gave rise to the desired natural product.