448961-10-2

Upstream product

• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 87420-26-6 (1R,2S,3R)-3-[N-Phenylsulfonyl-N-(3,5-dimethylphenyl)amino]bornan-2-ol 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 

Downstream Products

• 172588-54-4 (1R,2S,3R,4S)-<3--2-bornyl>-(1R,5S)-5-butyl-2-oxo-cyclopentanecarboxylate 
• 172588-55-5 (1R,2S,3R,4S)-<3--2-bornyl>-(1R,5S)-5-tert-butyl-2-oxo-cyclopentanecarboxylate 
• 448961-11-3 (2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate 
• 174757-25-6 5-Oxo-cyclopent-1-enecarboxylic acid (1R,2S,3R,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 

Relevant academic research and scientific papers

EPC synthesis of 5-substituted 2-oxo-cyclopentanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclopentenecarboxylates

Asymmetric shielded 2-oxo-cyclopentenecarboxylates 6n and 6x were prepared by trans-esterification of 2-oxo-cyclopentanecarboxylate 2 with camphor derived concave alcohols 1n and 1x and by subsequent introduction of a double bond via phenylselenides. Dias

A convergent synthesis of the cardenolide skeleton: Intramolecular aldol condensation via reduction of α-bromoketones

Synthesis of the highly biologically valuable cardenolide backbone was achieved via anionic polycyclization. Bromoketone 18, obtained from double-Michael cycloaddition between cyclohexenone 14 and γ,δ-unsaturated β-ketoester 16, was efficiently aldolized under reductive conditions. The highly functionalized tetracyclic compound 52 is an important synthetic intermediate that is potentially amenable to natural cardenolide total synthesis.

Enatiomerically pure 5-substituted 2-oxo-cyclopentanecarboxylates by conjugate addition of cuprates to asymmetry shielded 2-oxo-cyclopentenecarboxylates

Asymmetric shielded 2-oxo-cyclopentenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclopentanecarboxylate 2 with camphor derived concave alcohols 1n and 1x and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78°C and deprotection by ethanolysis gave enantiomerically pure 5-substituted 2-oxo-cyclopentanecarboxylates 13-18 and ent-13-18, valuable as chiral building blocks in natural product synthesis.