676345-33-8

Upstream product

• 13865-19-5 4-oxobutanoic acid methyl ester 
• 155795-48-5 (diethoxyphosphoryl)acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester 
• 71804-27-8 (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 
• 65253-04-5 (-)-8-phenylmenthol 

Downstream Products

• 167304-71-4 (R)-2-Oxo-5-phenyl-cyclopentanecarboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 913617-27-3 (2S,3R)-3-(4-Benzyloxy-1-methylene-butyl)-2-methyl-cyclopentanone 
• 913617-28-4 (1R,2S,3R)-3-(4-Benzyloxy-1-methylene-butyl)-1,2-dimethyl-cyclopentanol 
• 913617-24-0 (1S,2R)-2-(4-Benzyloxy-1-methylene-butyl)-5-oxo-cyclopentanecarboxylic acid methyl ester 
• 913617-26-2 (1R,2S)-2-(4-Benzyloxy-1-methylene-butyl)-1-methyl-5-oxo-cyclopentanecarboxylic acid methyl ester 
• 99877-51-7 4-(3-hydroxy-2,3-dimethyl-cyclopentyl)-pent-4-ene-1-ol 
• 64145-51-3 (R)-3-phenylcyclopentanone 
• 131235-66-0 methyl 2-oxo-5-phenylcyclopentanecarboxylate 
• 676345-40-7 (1S,2R)-2-tert-Butyl-5-oxo-cyclopentanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Total synthesis of (-)-chokol A by an asymmetric domino Michael addition-Dieckmann cyclization

A convergent and asymmetric total synthesis of (-)-chokol A was accomplished in six steps starting from the α,β-unsaturated ester (E)-9 in an overall yield of 27% with an enantiomeric excess of 95%. The key step of this synthesis is the asymmetric tandem conjugate addition-Dieckmann cyclization of the higher-order cuprate 8 derived from vinyl bromide 7 with the α,β-unsaturated ester (E)-9. Georg Thieme Verlag Stuttgart.

3-Substituted and 2,3-Disubstituted Cyclopentanones via an Asymmetric Tandem 1,4-Addition/Dieckmann Cyclization

A new stereoselective method for the synthesis of 3-substituted and 2,3-disubstituted cyclopentanones is described. The key step is the 1, 4-addition of a cuprate to a chilar Michael-acceptor derived from (-)-8-phenylmenthol or the Helmchen auxiliary followed by Dieckmann cyclization of the obtained chiral enolates. The resultant 2,3-cyclopentanones can be transformed after methanolysis and demethoxycarbonylation to the related 3-substituted cyclopentanones.