273381-22-9

Upstream product

• 273381-20-7 (1R,2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(1-methyl-1-phenyl-ethoxy)-cyclopentane-1,2-diol 
• 258834-31-0 tert-Butyl-dimethyl-[(1S,4R)-4-(1-methyl-1-phenyl-ethoxy)-cyclopent-2-enyloxy]-silane 
• 258834-27-4 (-)-cis-1-acetoxy-4-cumyloxy-2-cyclopentene 
• 258834-30-9 (-)-cis-4-Cumyloxy-2-cyclopenten-1-ol 
• 57702-56-4 cis- and trans-4-cumyloxy-2-cyclopentenol 
• 65457-77-4 4-<(1,1'-dimethylbenzyl)oxy>-2-cyclopentenone 
• 273381-21-8 tert-Butyl-[(3aS,4S,6R,6aS)-2,2-dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-yloxy]-dimethyl-silane 

Downstream Products

• 273381-24-1 (3aS,4R,6R,6aS)-2,2,4-Trimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 104010-72-2 (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 273381-23-0 (3aS,6R,6aS)-2,2-Dimethyl-6-(1-methyl-1-phenyl-ethoxy)-tetrahydro-cyclopenta[1,3]dioxol-4-one 

Relevant academic research and scientific papers

Chiral preparation of polyoxygenated cyclopentanoids

A series of polyoxygenated cyclopentanoids, including 2,2-dimethyl- 3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one, has been prepared in both enantiomeric forms from cyclopentadiene by employing lipase-mediated kinetic resolution as the key step. Thus, cyclopentadiene is first transformed into racemic cis-4-cumyloxycyclopent-2-en-1-ol which is resolved under transesterification conditions in the presence of lipase PS. After transformation into the corresponding tert-butyldimethylsilyl (TBS) ethers, each of the enantiomers is cis-dihydroxylated diastereoselectively from the less hindered face which is transformed into the 2,3-O-isopropylidene-1,4-di- O-protected (trans-1,2:cis-2,3:trans-3,4)-1,2,3,4-cyclopentanetetraol. Selective removal of the 1,4-protecting group gives the corresponding 2,3,4- O-protected cyclopentanols which are further transformed into the 2,3,4-O- protected cyclopentanones on oxidation without suffering β-elimination. Exposure of the cyclopentanones to warm acetic acid allows β-elimination to give rise to the dehydration product 2,2,-dimethyl-3a,6a-dihydro-4H- cyclopenta[d][1,3]dioxol-4-one having the corresponding chirality without losing their original chiral integrity.

An enantiodivergent route to α-cuparenone utilizing chiral cyclopentenol having a latent meso structure

An efficient enantiodivergent route to α-cuparenone, a sesquiterpene isolated in both enantiomeric forms, has been developed utilizing a chiral cyclopentanoid starting material having a latent meso structure. (C) 2000 Elsevier Science Ltd.