35135-35-4

Basic information

• Product Name: Sceletium a4
• Synonyms: Sceletium a4
• CAS NO: 35135-35-4
• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.42
• Mol File: 35135-35-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Sceletium a4(CAS DataBase Reference)
• NIST Chemistry Reference: Sceletium a4(35135-35-4)
• EPA Substance Registry System: Sceletium a4(35135-35-4)

Safety Data

• Hazardous Substances Data: 35135-35-4(Hazardous Substances Data)

Upstream product

• 216005-96-8 {2-[(R)-8-(3,4-Dimethoxy-phenyl)-6-[1,3]dioxolan-2-ylethynyl-1,4-dioxa-spiro[4.5]dec-6-en-8-yl]-ethyl}-methyl-carbamic acid methyl ester 
• 216005-97-9 {2-[(R)-8-(3,4-Dimethoxy-phenyl)-6-((Z)-2-[1,3]dioxolan-2-yl-vinyl)-1,4-dioxa-spiro[4.5]dec-6-en-8-yl]-ethyl}-methyl-carbamic acid methyl ester 
• 216005-90-2 {2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2-hydroxy-cyclohexyl]-ethyl}-methyl-carbamic acid methyl ester 
• 216005-98-0 {2-[(R)-8-(3,4-Dimethoxy-phenyl)-6-((Z)-2-[1,3]dioxolan-2-yl-vinyl)-1,4-dioxa-spiro[4.5]dec-6-en-8-yl]-ethyl}-methyl-amine 
• 77783-99-4 (+/-)-4-(3,4-dimethoxyphenyl)-2-<2-(5,5-dimethyl-1,3-dioxan-2-yl)ethyl>-4-formylmethylcyclohexan-1-one 2,2-dimethyltrimethylene acetal 
• 77783-97-2 (+/-)-4-allyl-4-(3,4-dimethoxyphenyl)-2-<2-(5,5-dimethyl-1,3-dioxan-2-yl)ethyl>cyclohexan-1-one 2,2-dimethyltrimethylene acetal 
• 77784-01-1 (+/-)-4-(3,4-dimethoxyphenyl)-2-<2-(5,5-dimethyl-1,3-dioxan-2-yl)ethyl>-4-(2-methylaminoethyl)cyclohexan-1-one 2,2-dimethyltrimethyllene acetal 
• 74-89-5 methylamine 
• 53400-41-2 5,6,7,8-tetrahydroquinolin-5-one 
• 207515-77-3 {3-[(R)-8-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]dec-6-en-6-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester 
• 207515-76-2 {3-[(R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-(3,4-dimethoxy-phenyl)-6-oxo-cyclohex-1-enyl]-prop-2-ynyl}-carbamic acid tert-butyl ester 
• 207515-79-5 (3-{(R)-8-(3,4-Dimethoxy-phenyl)-8-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-1,4-dioxa-spiro[4.5]dec-6-en-6-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester 
• 207515-80-8 ((Z)-3-{(R)-8-(3,4-Dimethoxy-phenyl)-8-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-1,4-dioxa-spiro[4.5]dec-6-en-6-yl}-allyl)-carbamic acid tert-butyl ester 
• 207515-68-2 Dithiocarbonic acid O-[(R)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(3,4-dimethoxy-phenyl)-2-oxo-cyclohexyl] ester S-methyl ester 

Downstream Products

• 93527-79-8 (+/-)-N-acetyltortuosamine 
• 79517-20-7 (±)-tortuosamine 

Relevant articles and documents

Efficient Synthesis of (?)-Corynoline by Enantioselective Palladium-Catalyzed α-Arylation with Sterically Hindered Substrates

Sterically hindered substrates can be employed in an enantioselective palladium-catalyzed α-arylation with the chiral monophosphorus ligand BI-DIME. This process enabled an efficient synthesis of the antidepressant (S)-nafenodone, a four-step enantioselective synthesis of the Sceletium alkaloid (+)-sceletium A-4, a concise five-step enantioselective synthesis of (?)-corynoline, as well as a three-step preparation of (?)-DeN-corynoline.

First enantiocontrolled synthesis of sceletium alkaloid A-4: Determination of the absolute configuration

Sceletium A-4, a pyridine alkaloid isolated from the Sceletium species, has been synthesized for the first time in an enantiocontrolled manner along with (-)-mesembrine, an alkaloid isolated from the same plant, starting from a chiral cyclohexadienone synthon to determine the absolute configuration.

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.

Applications of Substituted Arylacetaldehydes in the Total Synthesis of Mesembrane Alkaloids. Part 2. An Alternative Systhesis of (+/-)-Sceletium Alkaloid A4

The substituted arylacetaldehydes (+/-)-2-(3,4-dimethoxyphenyl)pent-4-enal (1c) is shown to serve as a precursor in the total synthesis of the mesembrane alkaloid (+/-)-sceletium alkaloid A4.