211426-28-7

Upstream product

• 98-79-3 L-Pyroglutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 
• 211426-26-5 (S)-2-Formyl-5-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 195964-54-6 1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate 
• 188200-05-7 1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 211426-27-6 (S)-2-(1-Hydroxy-3-phenyl-prop-2-ynyl)-5-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 211426-30-1 (S)-2-(3-Phenyl-prop-2-ynyl)-5-phenylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 211426-31-2 (1R,4S)-2-[1-Phenyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 163513-98-2 (-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 211426-29-8 (S)-2-Methoxy-5-(3-phenyl-prop-2-ynyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Formal synthesis of natural epibatidine and of its enantiomer: Use of radical cyclization in an enantiospecific route

(S)-Pyroglutamic acid was converted into the (phenylthio)acetylene 14, which undergoes radical cyclization to the 7-azabicyclo[2.2.1]heptane 15. Ozonolysis then affords ketone 4, a synthetic precursor of (-)-epibatidine.