74163-89-6

Basic information

• Product Name: (-)-joubertinamine
• Synonyms: (-)-joubertinamine
• CAS NO: 74163-89-6
• Molecular Weight: 291.39
• Mol File: 74163-89-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (-)-joubertinamine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-joubertinamine(74163-89-6)
• EPA Substance Registry System: (-)-joubertinamine(74163-89-6)

Safety Data

• Hazardous Substances Data: 74163-89-6(Hazardous Substances Data)

Upstream product

• 4746-97-8 cyclohexanedione monoethylene ketal 
• 2859-78-1 4-Bromoveratrole 
• 70779-49-6 4,4-ethylenedioxy-1-(3',4'-dimethoxyphenyl)cyclohexene 
• 593-51-1 methylamine hydrochloride 
• 1154488-66-0 2-((1R,4S)-1-(3,4-dimethoxyphenyl)-4-hydroxycyclohex-2-enyl)acetaldehyde 
• 86227-37-4 N-benzenesulfonyl 4-(3',4'-dimethoxyphenyl)-4-methylaminoethylcyclohex-2-en-1-one 
• 85753-65-7 N-[3-Cyano-3-(3,4-dimethoxy-phenyl)-propyl]-N-methyl-benzenesulfonamide 
• 86227-35-2 N-[3-(3,4-Dimethoxy-phenyl)-4-oxo-butyl]-N-methyl-benzenesulfonamide 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 70779-54-3 Acetic acid (7R,8S)-8-(3,4-dimethoxy-phenyl)-8-(2-oxo-ethyl)-1,4-dioxa-spiro[4.5]dec-7-yl ester 
• 70779-53-2 Acetic acid (7R,8S)-8-allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]dec-7-yl ester 
• 121537-77-7 (1RS,2SR)-5,5-ethylenedioxy-2-(N-methylamidomethyl)-2-(3',4'-dimethoxyphenyl)cyclohexyl acetate 
• 121537-78-8 [(7R,8S)-7-Acetoxy-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-acetic acid methyl ester 
• 121537-76-6 2-carboxymethyl-5,5-ethylenedioxy-2-(3',4'-dimethoxyphenyl)cyclohexyl acetate 

Downstream Products

• 468-53-1 (-)-mesembrine 
• 71610-13-4 (+/-)-N,O-diacetyljoubertinamine 

Relevant articles and documents

Consecutive sigmatropic rearrangements in the enantioselective total synthesis of (-)-joubertinamine and (-)-mesembrine

Joubertinamine and mesembrine are two related alkaloids isolated from Sceletium plants. From the perspective of chemical synthesis, the major challenge posed by joubertinamine and mesembrine is undoubtedly the construction of the benzylic quaternary stere

Opening of aryl-substituted epoxides to form quaternary stereogenic centers: Synthesis of (-)-mesembrine

Cycloalkanones are easily converted into aryl-substituted cyclic alkenes by the addition of an aryl Grignard reagent followed by dehydration. These alkenes are good substrates for asymmetric epoxidation. We have found that the addition of allylic and benzylic Grignard reagents can occur preferentially at the benzylic position of the derived epoxides to give the quaternary stereogenic center. This approach led to a short synthesis of the nanomolar serotonin re-uptake inhibitor (-)-mesembrine.

SCELETIUM (AIZOACEAE) ALKALOIDS: TOTAL SYNTHESIS OF RACEMIC MESEMBRANONE, JOUBERTINAMINE AND EPIJOUBERTINAMINE

The total synthesis of the Sceletium alkaloids mesembranone, joubertinamine and epijoubertinamine via the intramolecular cyclization of an enone to a benzensulfonamide grouping under the conditions of a dissolving metal reduction is described.