189363-85-7

Upstream product

• 109380-07-6 2-bromocyclohex-2-en-1-ol 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 216005-81-1 3-Chloro-benzoic acid 2-(3,4-dimethoxy-phenyl)-cyclohex-2-enyl ester 
• 27124-93-2 1-(3,4-dimethoxyphenyl)cyclohexene 

Downstream Products

• 189364-06-5 Carbonic acid 2-(3,4-dimethoxy-phenyl)-cyclohex-2-enyl ester methyl ester 
• 189363-86-8 N-allyl-2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-ylamine 
• 216006-07-4 Acetic acid (R)-2-(3,4-dimethoxy-phenyl)-cyclohex-2-enyl ester 
• 216006-01-8 (-)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-ol 
• 189364-02-1 (3R,3aS,7aS)-1-(p-tolylsufonyl)-3-{[(methoxycarbonyl)oxy]methyl}-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole 
• 189364-03-2 (3R,3aS,7aS)-1-(p-tolylsufonyl)-3-(hydroxymethyl)-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole 
• 189364-04-3 (3R,3aS,7aS)-1-(p-tolylsufonyl)-3-formyl-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole 
• 189364-01-0 Carbonic acid (3R,3aS,7aS)-3a-(3,4-dimethoxy-phenyl)-6-oxo-1-(toluene-4-sulfonyl)-octahydro-indol-3-ylmethyl ester methyl ester 
• 189364-00-9 Carbonic acid (3R,3aS,7aS)-3a-(3,4-dimethoxy-phenyl)-6-oxo-1-(toluene-4-sulfonyl)-2,3,3a,6,7,7a-hexahydro-1H-indol-3-ylmethyl ester methyl ester 
• 189363-98-2 (3R,3aS,7aS)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-3a-(3,4-dimethoxy-phenyl)-1-(toluene-4-sulfonyl)-2,3,3a,6,7,7a-hexahydro-1H-indole 
• 189363-93-7 (3R,3aS,7aS)-1-Benzhydryl-3-(tert-butyl-dimethyl-silanyloxymethyl)-3a-(3,4-dimethoxy-phenyl)-2,3,3a,6,7,7a-hexahydro-1H-indole 
• 189363-99-3 Carbonic acid (3R,3aS,7aS)-3a-(3,4-dimethoxy-phenyl)-1-(toluene-4-sulfonyl)-2,3,3a,6,7,7a-hexahydro-1H-indol-3-ylmethyl ester methyl ester 
• 189364-05-4 (3aS,7aS)-1-(p-tolylsufonyl)-3a-(3,4-dimethoxyphenyl)-6,6-(ethylenedioxy)-2,3,3a,4,5,6,7,7a-octahydroindole 
• 189363-94-8 [(3R,3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-1-(toluene-4-sulfonyl)-2,3,3a,6,7,7a-hexahydro-1H-indol-3-yl]-methanol 

Relevant academic research and scientific papers

Asymmetric synthesis of sceletium alkaloids: (-)-Mesembrine, (+)- sceletium a-4, (+)-tortuosamine and (+)-N-formyltortuosamine

Three procedures for the transformation of achiral 1-(3,4- dimethoxyphenyl)cyclohexene into enantiomerically pure 2-(3,4- dimethoxyphenyl)cyclohex-2-en-1-o1 have been established at first. Utilizing the (-)-cyclohexenol thus obtained, the four titled Sceletium alkaloids have been synthesized in the natural enantiomeric forms.

Total syntheses of (-)-mesembrane and (-)-mesembrine via palladium-catalyzed enantioselective allylic substitution and zirconium-promoted cyclization

4-Arylhexahydroindole derivatives 5 were synthesized from 2-arylcyclohexenyl allylamine derivatives 4, which have a large protecting group on nitrogen, using zirconium-promoted cyclization. Reaction of 4e with Cp2ZrBu2, followed by treatment with MeMgBr and then O2, gave 2a in 63% yield by a one-pot reaction, since the approach of O2 to zirconium was prevented by the aryl group. The total syntheses of (+)-mesembrane and (+)-mesembrine were achieved starting from 2a. To synthesize these natural products in a chiral form, the starting allylamine derivative 24 (80% yield, 86% ee, recrystallized from MeOH, 99% ee with 79% recovery) was prepared from allyl carbonate 22a and N-tosylallylamine 23 using palladium-catalyzed asymmetric amination in the presence of (S)-BINAPO as a chiral ligand. (-)-Mesembrane and (-)-mesembrine were synthesized from this allylamine 24.