205675-73-6

Upstream product

• 108-05-4 vinyl acetate 
• 205675-68-9 cis-4-carbobenzoxyamino-2-cyclopentenol 
• 501-53-1 benzyl chloroformate 
• 99027-88-0 N-(benzyloxycarbonyl)-2-oxa-3-azabicyclo<2.2.1>hept-5-ene 
• 542-92-7 cyclopenta-1,3-diene 
• 3426-71-9 Benzyl N-hydroxycarbamate 

Downstream Products

• 221910-76-5 (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol 
• 73903-33-0 (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid 
• 115890-53-4 1-(benzyloxycarbonyl)kainic acid dimethyl ester 
• 120229-02-9 (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 302906-13-4 [(1R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-2-enyl]-carbamic acid benzyl ester 
• 302906-15-6 ((3aS,4R,6S,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester 
• 302906-17-8 (3aS,3bR,6S,6aS,7aR)-6-Isopropenyl-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester 
• 302906-14-5 [(3aS,4R,6S,6aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-carbamic acid benzyl ester 
• 302906-16-7 Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester 

Relevant academic research and scientific papers

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.

Enzymatic resolution of aminocyclopentenols as precursors to D- and L- carbocyclic nucleosides

Racemic cis-4-aminocyclopent-2-en-1-ols were synthesized in three steps utilizing hetero Diels-Alder chemistry. Starting from suitably protected hydroxylamines, oxidization with sodium periodate and trapping with cyclopentadiene afforded cycloadducts (±)-5a-d. The N-O bond of the cycloadducts was reduced with Mo(CO)6 to afford (±)-cis-4-aminocyclopent- 2-en-1-ols (±)-6a-d. These compounds, or their corresponding acetates, were kinetically resolved by enzymatic acetylation of hydrolysis, respectively. Enzymatic acetylation of cis-N-(benzylcarbamoyl)-4-aminocylopent-2-enol [(±)-6a] with Candida antarctica B lipase and Pseudomonas species lipase gave the corresponding acetate (-)-7a in 90% and 92% ee, respectively, after 40% conversion. Enzymatic hydrolysis of cis-N-acetyl-4-aminocyclopent-2-enol 1-O-acetate (±)-7d with electric eel acetylcholine esterase was successful in providing both cis-N-acetyl-4-aminocyclopent-2-enols (+)-6d and (+)-7d in 92% ee (99% ee after a single recrystallizaton) after 40% conversion. Further synthetic transformation of these resolved synthetic building blocks and derivatives are also reported.