222022-91-5

Upstream product

• 328533-38-6 (1'S)-2-Bromo-3,4-dimethoxy-5-(1',2',2'-trimethylcyclopentyl)phenyl-1-methanol 
• 223751-48-2 (1'S)-1-bromo-2,3-dimethoxy-6-methyl-4-(1',2',2'-trimethylcyclopentyl)benzene 
• 222022-93-7 (1'S)-1,2-dimethoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)benzene 
• 222022-92-6 (1'S)-3,4-dimethoxy-5-(1',2',2'-trimethylcyclopentyl)benzyl alcohol 
• 304859-87-8 (1'S)-2-Bromo-3,4-dimethoxy-5-(1',2',2'-trimethylcyclopentyl)benzaldehyde 
• 77-78-1 dimethyl sulfate 
• 185967-11-7 (1'S)-3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzaldehyde 

Downstream Products

• 222022-93-7 (1'S)-1,2-dimethoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)benzene 
• 333401-67-5 [2,3-Dimethoxy-6-methyl-4-((S)-1,2,2-trimethyl-cyclopentyl)-phenyl]-[3,4-dimethoxy-5-((S)-1,2,2-trimethyl-cyclopentyl)-phenyl]-methanol 
• 185967-11-7 (1'S)-3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzaldehyde 
• 118584-11-5 (-)-mastigophorene C 
• 118584-12-6 (-)-mastigophorene D 
• 333401-68-6 1,2-bis[5'-((1S)-1,2,2-trimethylcyclopentyl)-3',4'-dimethoxyphenyl]ethane 
• 333401-69-7 (1''S,1'''S)-4,5'-bis(1,2,2-trimethylcyclopentyl)-6-methyl-2,3,3',4'-tetramethoxy-diphenylmethane 
• 405063-84-5 3,3'-Dimethoxy-6,6'-dimethyl-4,4'-bis-((S)-1,2,2-trimethyl-cyclopentyl)-biphenyl-2,2'-diol 
• 222022-97-1 1-Benzyloxy-2-isopropoxy-5-methyl-3-((S)-1,2,2-trimethyl-cyclopentyl)-benzene 
• 222022-96-0 1-Benzyloxy-2-ethoxy-5-methyl-3-((S)-1,2,2-trimethyl-cyclopentyl)-benzene 
• 222022-89-1 2-Ethoxy-5-methyl-3-((S)-1,2,2-trimethyl-cyclopentyl)-phenol 
• 304859-84-5 (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-5-(1'',2'',2''-trimethylcyclopentyl)-3,4-(diphenylmethylidenedioxy)benzoate 
• 304859-85-6 (1'S,1''S)-4-methoxy-3,8-di(1,2,2,-trimethylcyclopentyl)-1-methyl-9,10(diphenylmethylidenedioxy)-dibenzo[b,d]pyran-6-one 
• 304859-79-8 (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate 

Relevant academic research and scientific papers

From dynamic to non-dynamic kinetic resolution of lactone-bridged biaryls: Synthesis of mastigophorene B

The atroposelective ring cleavage of configurationally unstable biaryl lactones, by dynamic kinetic resolution, is an efficient tool for the stereoselective synthesis of axially chiral biaryl target molecules. The recent extension of this methodology to the kinetic resolution of configurationally stable biaryl lactones and its application to natural product synthesis is described herein, exemplarily for the preparation of the nerve-growth stimulating dimeric sesquiterpene mastigophorene B.

First total synthesis of the mastigophorenes C and D and of simplified unnatural analogs

The first total synthesis of the mastigophorenes C (2) and D (3), natural 'dimeric' sesquiterpenes isolated from the liverwort Mastigophora diclados with interesting biological activities, is described. As previously for mastigophorenes A (1) and B, the divergent synthetic approach was first optimized on a simplified model system with a tert-butyl group instead of the chiral cyclopentyl residue, also in order to find more easily available compounds with similar or even improved biological activity.

Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B

The stereoselective total synthesis of the sesquiterpene herbertenediol (3) and of its naturally occurring dimers, mastigophorenes A [(P)-1] and B [(M)-1], is described. Following the 'lactone concept', the configuration at the biaryl axis was atropo-dive

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.