219143-77-8

Upstream product

• 5162-44-7 1-bromo-4-butene 
• 219143-76-7 (3aS,7aS)-2-(3,4-Dimethoxy-benzyl)-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 81316-62-3 ethyl 2-(3,4-dimethoxyphenyl)acetoimidate hydrochloride 

Downstream Products

• 219143-78-9 N-[3-(3,4-dimethoxy-phenyl)-3-(3a,4,5,6,7,7a-hexahydro-1H-benzoimidazol-2-yl)-hept-6-enyl]-N-methyl-benzenesulfonamide 
• 219143-75-6 N-{2-[1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-N-methyl-benzenesulfonamide 
• 219143-74-5 N-[3-(3,4-dimethoxy-phenyl)-3-formyl-6-oxo-heptyl]-N-methyl-benzenesulfonamide 
• 219143-73-4 N-[3-(3,4-dimethoxy-phenyl)-3-formyl-hept-6-enyl]-N-methyl-benzenesulfonamide 
• 468-53-1 (-)-mesembrine 

Relevant academic research and scientific papers

A concise synthesis of (-)-mesembrine

(-)-Mesembrine 11 was synthesized in 7 steps, in 19.4% overall yield and with ee>95%. The key step of the sequence is a stereoselective alkylation reaction of dianion derived from C2 symmetric imidazolines allowing efficient formation of quaternary benzylic center. Chiral auxiliaries derived from (S,S)-1,2-diamino-1,2-diphenylethane 1a and (S,S)-1,2-diaminocyclohexane 1b were compared. This synthesis provided unambiguous correlation of the newly formed stereocenter.