189364-06-5

Upstream product

• 79-22-1 methyl chloroformate 
• 189363-85-7 2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-ol 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 109380-07-6 2-bromocyclohex-2-en-1-ol 

Downstream Products

• 189364-07-6 N-Allyl-N-[(S)-2-(3,4-dimethoxy-phenyl)-cyclohex-2-enyl]-4-methyl-benzenesulfonamide 
• 244250-95-1 (S)-2-(3,4-dimethoxyphenyl)-3-[(N-p-tolylsulfonyl)-2,2-diethoxyethylamino]-1-cyclohexene 
• 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 
• 189363-92-6 [(3R,3aS,7aS)-1-Benzhydryl-3a-(3,4-dimethoxy-phenyl)-2,3,3a,6,7,7a-hexahydro-1H-indol-3-yl]-methanol 
• 189364-20-3 [(3R,3aS,7aS)-3a-(3,4-Dimethoxy-phenyl)-1-(toluene-4-sulfonyl)-octahydro-indol-3-yl]-methanol 

Relevant academic research and scientific papers

Palladium-Catalyzed Asymmetric Allylic Substitution of 2-Arylcyclohexenol Derivatives: Asymmetric Total Syntheses of (+)-Crinamine, (-)-Haemanthidine, and (+)-Pretazettine

Much interest has been shown in Amaryllidaceae alkaloids as synthetic targets due to their wide range of biological activities. Over 100 alkaloids have been isolated from members of the Amaryllidaceae family; most of them can be classified into eight skel

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.