928065-01-4

Upstream product

• 928065-02-5 (2S,3R,4R)-3-hydroxy-4-iodo-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenyl methyl) ester 
• 120104-68-9 methyl 2-(benzyloxyimino)acetate 
• 501-53-1 benzyl chloroformate 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 928065-03-6 (2S,4S)-4-iodo-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester 
• 5211-24-5 (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester 
• 928065-04-7 (1R,2S,5S)-6-oxa-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-methyl 3-(phenylmethyl) ester 
• 51-35-4 4R-4-hydroxyproline 

Relevant academic research and scientific papers

Total synthesis of penmacric acids via an intermolecular radical addition reaction

The total syntheses of penmacric acid and its three stereoisomers were accomplished through the intermolecular radical addition reaction of the 4-pyrrolidyl radical derived from trans-4-hydroxy-l-proline. Furthermore, 1′,3-diepi-penmacric acid was synthesized stereoselectively via double stereoinduction in the radical reaction.

First total synthesis of penmacric acid and its stereoisomer

The total synthesis of penmacric acid and its stereoisomer, epipenmacric acid, is reported for the first time starting from trans-4-hydroxy-l-proline. Et3B-induced diastereoselective radical addition reaction was used to control stereoselectivity at the C3 stereogenic center as a key step.