162489-18-1

Usage

InChI:InChI=1/C8H12O3/c1-8(7(10)11-2)5-3-4-6(8)9/h3-5H2,1-2H3/t8-/m1/s1

Upstream product

• 139685-42-0 methyl (1R)-2-<(2R,3R)-3-hydroxybutan-2-yl>oxy-1-methyl-2-cyclopenten-1-carboxylate 
• 122331-04-8 methyl (1R,2S)-2-hydroxy-1-methylcyclopentanecarboxylate 
• 138200-47-2 N-(2-carbomethoxy-1-cyclopenten-1-yl)-(S)-valine tert-butyl ester 
• 74-88-4 methyl iodide 
• 122249-17-6 S-ethyl (1R,2S)-2-hydroxycyclopentanecarboxylthioate 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 30680-84-3 methyl 1-methyl-2-oxocyclopentane-1-carboxylate 
• 122331-02-6 (1S,2R)-2-(Methoxycarbonyl)cyclopentan-1-ol 

Downstream Products

• 81784-10-3 4-methyl-2-[(1S)-1,2,2-trimethylcyclopentyl]phenol 
• 86996-95-4 (S)-5-methyl-3-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol 
• 124424-22-2 (-)-mastigophorene B 
• 81784-13-6 (1S)-1,2,2-trimethyl-1-(2-methoxy-5-methyl)phenylcyclopentane 
• 325726-91-8 1,2-dimethyl-1-hydroxymethyl-2-(2-hydroxy-5-methylphenyl)cyclopentane 
• 369610-41-3 1,1,2-trimethyl-2-(2-methoxymethyloxy-5-methylphenyl)cyclopentane 
• 369610-38-8 1,2-dimethyl-1-formyl-2-(2-methoxy-5-methylphenyl)cyclopentane 
• 369610-30-0 2-iodo-4-methylphenyl 1,2-dimethyl-2-cyclopentenecarboxylate 
• 369610-36-6 (1R,2S)-1-(hydroxymethyl)-2-(2-methoxy-5-methylphenyl)-1,2-dimethylcyclopentane 
• 369610-42-4 1,1,2-trimethyl-2-(3-hydroxy-2-methoxymethyloxy-5-methylphenyl)cyclopentane 

Relevant academic research and scientific papers

Catalytic asymmetric intramolecular homologation of ketones with α-diazoesters: Synthesis of cyclic α-Aryl/Alkyl β-ketoesters

A catalytic asymmetric intramolecular homologation of simple ketones with α-diazoesters was firstly accomplished with a chiral N,N′-dioxide-Sc(OTf)3 complex. This method provides an efficient access to chiral cyclic α-aryl/alkyl β-ketoesters containing an all-carbon quaternary stereocenter. Under mild conditions, a variety of aryl- and alkyl-substituted ketone groups reacted with α-diazoester groups smoothly through an intramolecular addition/rearrangement process, producing the β-ketoesters in high yield and enantiomeric excess.

Total syntheses of neuroprotective mastigophorenes A and B

(-)-Herbertenediol (3) which is regarded as a biosynthetic precursor of mastigophorenes A and B has been effectively synthesized from (R)-1,2-dimethyl-2-cyclopentene carboxylic acid by applying an intramolecular Heck reaction to the construction of the quaternary carbon center, and then horseradish peroxidase-catalyzed oxidative coupling of 3 has given rise to (-)-mastigophorenes A and B. Mastigophorenes A and B have been found to exhibit significant neuroprotective activity in primary cultures of fetal rat cortical neurons.

Total synthesis of herbertenediol, an isocuparane sesquiterpene isolated from liverworts

Total synthesis of herbertenediol, an isocuparane-sesquiterpene possessing a potent anti-lipid peroxidation activity isolated from a liverwort, has been achieved via herbertenol using intramolecular Heck reaction as the key step.

Chiral Synthesis via Organoboranes. 42. Selective Reductions. 57. Efficient Kinetic Resolution of Representative α-Tertiary Ketones with B-Chlorodiisopinocampheylborane

Kinetic resolution of racemic α-tertiary ketones with 0.5-0.6 molar equiv of B-chlorodiisopinocampheylborane provides the product alcohols in very high diastereomeric and enantiomeric excess, with the unreacted ketone recovered in very high ee.For example, ethyl 1-methyl-2-oxocyclopentane- and cyclohexanecarboxylates are partially reduced to recover the ketone in 91 to >/=99percent ee and the product alcohols in up to 94percent de, with >90percent ee for the major diastereomer.Bicyclic ketones, such as 1-methyl- and 1-ethylnorcamphor, camphor, and camphenilone, are readily resolved to provide the ketone in 92 to >/=99percent ee, with the product alcohol recovered in high de and ee.Dihydrospirooctane-2,2'(3'H)-furan>-3-one is resolved to provide the ketone in >/=99percent ee and the product alcohol in >/=99percent de.In all the cases studied, the R-isomer of the ketone is recovered when dIpc2BCl is used for kinetic resolution, while lIpc2BCl provides the S-ketone.Optimum conditions for obtaining the product alcohol, or the ketone, or both, in very high yields and ee have been established.

Asymmetric Alkylation Using Chiral Cyclic Diols to Prepare a Quaternary Carbon

Asymmetric alkylation of cyclic and acyclic β-keto ester acetals (4, 5, 13, 14, and 18) with C2-symmetric cycloalkane-1,2-dioxy moiety proceeded in a highly diastereoselective manner to afford enol ethers (9-12, 15-17, 19a-c) with a chiral quat

Asymmetric Syntheses of (-)-Malyngolide and (-)-Frontalin by Utilizing Bakers' Yeast Reduction of S-Ethyl 2-Cyclopentanonecarboxylthioate

Bakers' yeast reduction of S-ethyl 2-cyclopentanonecarboxylthioate affords optically pure S-ethyl (1R,2S)-2-hydroxycyclopentanecarboxylthioate which is stereoselectively converted into (-)-malyngolide and (-)-frontalin.