124424-22-2

Upstream product

• 86996-95-4 (S)-5-methyl-3-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol 
• 223751-32-4 (S)-2-[2-Bromo-3,4-dimethoxy-5-((S)-1,2,2-trimethyl-cyclopentyl)-phenyl]-4-tert-butyl-4,5-dihydro-oxazole 
• 223751-41-5 (R)-2-[2-Bromo-3,4-dimethoxy-5-((S)-1,2,2-trimethyl-cyclopentyl)-phenyl]-4-isopropyl-4,5-dihydro-oxazole 
• 223751-40-4 (1'S)-2-bromo-3,4-dimethoxy-5-(1',2',2'-trimethylcyclopentyl)benzoic acid 
• 223751-48-2 (1'S)-1-bromo-2,3-dimethoxy-6-methyl-4-(1',2',2'-trimethylcyclopentyl)benzene 
• 223751-39-1 (R)-4-(2,3-dimethoxy-5-methylphenyl)-4,5,5-trimethylcyclopent-2-enone 
• 222022-93-7 (1'S)-1,2-dimethoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)benzene 
• 369610-42-4 1,1,2-trimethyl-2-(3-hydroxy-2-methoxymethyloxy-5-methylphenyl)cyclopentane 
• 369610-36-6 (1R,2S)-1-(hydroxymethyl)-2-(2-methoxy-5-methylphenyl)-1,2-dimethylcyclopentane 

Relevant academic research and scientific papers

Penicillium sclerotiorum catalyzes the conversion of herbertenediol into its dimers: Mastigophorenes A and B

Herbertenediol was subjected to biotransformation by Penicillium sclerotiorum. Spectral data analysis of the converted metabolites revealed that the neurotrophic active compounds, mastigophorenes A and B, dimeric to the substrate were formed.

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 syntheses of (-)-herbertenediol, (-)-mastigophorene A, and (-)- mastigophorene B. Combined utility of chiral bicyclic lactams and chiral aryl oxazolines

A nonracemic bicyclic lactam has been used to construct a chiral cyclopentane containing vicinal quaternary carbon centers in optically pure form, which is common to all of the title compounds. An oxazoline-mediated asymmetric Ullmann coupling was then utilized to establish chirality about the biaryl axis of mastigophorenes A and B. Through the course of this synthesis, it was clearly demonstrated that smaller chiral auxiliaries lead to higher levels of atroposelection, a previously unknown phenomenon of the asymmetric Ullmann coupling.