405063-84-5

Upstream product

• 222022-88-0 (1'S)-2-methoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)phenol 
• 86996-95-4 (S)-5-methyl-3-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol 
• 185967-11-7 (1'S)-3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzaldehyde 
• 222022-93-7 (1'S)-1,2-dimethoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)benzene 
• 222022-91-5 (1'S)-3,4-Dimethoxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde 
• 222022-92-6 (1'S)-3,4-dimethoxy-5-(1',2',2'-trimethylcyclopentyl)benzyl alcohol 
• 222022-94-8 (1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol 
• 222022-95-9 (1'S)-3-benzyloxy-4-methoxy-5-(1',2',2'-trimethylcyclopentyl)toluene 

Downstream Products

• 124424-22-2 (-)-mastigophorene B 

Relevant academic research and scientific papers

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.

First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol

The first synthesis of mastigophorenes A and B by oxidative phenolic coupling of partially protected derivatives of their joint natural monomeric half, herbertenediol, is described. The synthesis starts from this diol itself or from the corresponding aldehyde, both available by isolation from the liverwort, Herbertus aduncus. After transformation of herbertenediol to a chemically appropriate monophenolic coupling precursor, the oxidative dehydrodimerization was brought about using (tert-BuO)2, followed by deprotection to give mastigophorenes A and B in their 'natural' atropisomeric ratio, as isolated from the liverwort.