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
• Article Data: 4

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

• 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 
• 207515-81-9 {(Z)-3-[(R)-8-(2-tert-Butoxycarbonylamino-ethyl)-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]dec-6-en-6-yl]-allyl}-carbamic acid tert-butyl ester 
• 207515-66-0 (R)-9-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-(3,4-dimethoxy-phenyl)-1,5-dithia-spiro[5.5]undecan-7-one 
• 207515-67-1 (R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(3,4-dimethoxy-phenyl)-2,2-dimethoxy-cyclohexanol 
• 207515-75-1 (R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(3,4-dimethoxy-phenyl)-2-iodo-cyclohex-2-enone 
• 207515-65-9 (R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-(3,4-dimethoxy-phenyl)-cyclohexanone 
• 207515-69-3 (R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-(3,4-dimethoxy-phenyl)-cyclohex-2-enone 
• 207515-78-4 {3-[(R)-8-(3,4-Dimethoxy-phenyl)-8-(2-hydroxy-ethyl)-1,4-dioxa-spiro[4.5]dec-6-en-6-yl]-prop-2-ynyl}-carbamic acid tert-butyl ester 

Downstream Products

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

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.

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.