80233-00-7

Upstream product

• 80232-98-0 (E)-2-((E)-But-2-enyl)-2-(3,4-dimethoxy-phenyl)-hex-4-enoic acid 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 80232-99-1 3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-(1-iodo-ethyl)-dihydro-furan-2-one 

Downstream Products

• 80233-01-8 3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-5-hydroxy-dihydro-furan-2-one 
• 80233-05-2 4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone 
• 80233-03-0 3-(3,4-Dimethoxy-phenyl)-3-(3-oxo-butyl)-dihydro-furan-2-one 
• 80233-04-1 (S)-3a-(3,4-Dimethoxy-phenyl)-3,3a,4,5-tetrahydro-2H-benzofuran-6-one 
• 80233-02-9 3-((E)-But-2-enyl)-3-(3,4-dimethoxy-phenyl)-dihydro-furan-2-one 
• 6023-73-0 mesembrine 
• 80287-15-6 3a-(3,4-dimethoxyphenyl)-1-methyl-3,3a,4,5-tetrahydro-1H-indol-6(2H)-one 
• 174418-89-4 {2-[3-(3,4-Dimethoxy-phenyl)-2-hydroxy-5-(1-hydroxy-ethyl)-tetrahydro-furan-3-yl]-ethyl}-methyl-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

A new synthesis of (-)-mesembrine employing sharpless AD reaction and new radical-initiated reaction

Sharpless asymmetric dihydroxylation (AD reaction) of a σ-symmetric ethyl α,α-di[(E)-2-butenyl](3,4-dimethoxyphenyl)acetate allows an asymmetric construction of a quaternary carbon center by diastereoselective formation of the γ-lactone in moderate optical yields when double dihydroxylation occurs. The lactone generated is transformed into a Sceletium alkaloid (-)-mesembrine by discovery of the unprecedented radical-initiated cleavage reaction.

ANOTHER SYNTHESIS OF (+/-)-MESEMBRINE USING A SYMMETRIC STARTING MATERIAL

(+/-)-Mesembrine (10) has been synthesized efficiently via the vinylanalogous amide (9) using the symmetric substrate (1) as starting material.