21104-34-7

Upstream product

• 87014-19-5 (3aR,7aR)-3a-(3,4-Dimethoxy-phenyl)-hexahydro-benzofuran-2,6-dione 
• 74-89-5 methylamine 
• 87014-23-1 [1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-acetyl chloride 
• 25924-29-2 1-methyl-3a-(3,4-dimethoxyphenyl)-3,3a,4,5-tetrahydroindole-2,6(1H)-dione 
• 99706-75-9 3--2-(3,4-dimethoxyphenyl)prop-2-en-1-al 
• 58489-52-4 N-methyl-3-(3,4-dimethoxyphenyl)succinimide 
• 87014-17-3 Acetic acid (1R,3S,6S)-6-(3,4-dimethoxy-phenyl)-8-oxo-bicyclo[4.2.0]oct-3-yl ester 
• 91-16-7 1,2-dimethoxybenzene 
• 20036-53-7 3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one 
• 2859-78-1 4-Bromoveratrole 
• 80515-90-8 2-oxo-3a-<3,4-(dimethoxy)phenyl>-2,3,3a,4,5,7a-hexahydroindole 
• 80515-92-0 <β-3-<3,4-(dimethoxy)phenyl>cyclohex-2-enyl>acetic acid 
• 80515-95-3 N-hydroxy-2-oxo-3a-<3,4-(dimethoxy)phenyl>-2,3,3a,4,5,7a-hexahydroindole 
• 80515-98-6 N-methyl-2-oxo-3a-<3,4-(dimethoxy)phenyl>-6-hydroxy-7-bromo-2,3,3a,4,5,6,7,7a-octahydroindole 

Downstream Products

• 6023-73-0 mesembrine 
• 80515-96-4 C₁₉H₂₅NO₅ 

Relevant academic research and scientific papers

A Concise Total Synthesis of (±)-Mesembrine

A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson-Claisen rearra

Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: Enantioselective total synthesis of (-)-mesembrine

A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).

Allyl vinyl ethers via Wittig olefination: A short and efficient synthesis of (±)-mesembrine

A Wittig olefination-Claisen rearrangement approach has been successfully applied to a short and efficient synthesis of (±)-mesembrine.

[4 + 1] cycloaddition of bis(alkylthio)carbenes with vinyl isocyanates. Total synthesis of (±)-mesembrine

(matrix presented) The Sceletium alkaloid mesembrine has been synthesized in 13% overall yield by a sequence featuring a [4 + 1] cycloaddition of a bis-(alkylthio)carbene with a functionalized vinyl isocyanate.

INTRAMOLECULAR CYCLIZATION OF ALLYLSILYL SUBSTITUTED N-ACYLIMINIUM IONS. ACCESS TO 1- AND 2-AZABICYCLOALKANES. TOTAL SYNTHESIS OF (+/-)-MESEMBRINE

Access to 1- and 2-azabicycloalkanes by intramolecular cyclization of allylsilanes on α-acyliminium ions is described.This methodology is also used to achieve a highly stereoselective total synthesis of (+/-)-mesembrine.

A Synthesis of Seco-mesembrane Alkaloids, (+/-)-Joubertiamine, (+/-)-Joubertinamine, and (+/-)-Epijoubertinamine

A synthesis of seco-mesembrane alkaloids, (+/-)-joubertiamine (4), (+/-)-joubertinamine (5), and (+/-)-epijoubertinamine (6), was accomplished starting with 2-allyl-2-aryl-5,5-ethylenedioxycyclohexanones (10 and 3), which are readily available by allylati

CYCLISATION OF ALLYL SILANES. FORMAL TOTAL SYNTHESIS OF (+/-)-MESEMBRINE

The intramolecular reaction of an α-acyl iminium ion with an allyl silane occurs under non acidic conditions to afford the key intermediate 8 for the synthesis of (+/-)-mesembrine 1 in a stereospecific manner.

Total Syntheses of (+/-)-Mesembrine, (+/-)-Joubertinamine, and (+/-)-N-Demethylmesembrenone

The syntheses of three members of the sceletium alkaloid family are developed from a common synthon, leading to short, high-yielding stereorational routes to (+/-)-mesembrine, (+/-)-joubertinamine, and (+/-)-N-demethylmesembrenone.The latter is synthesize

Alkaloid Synthesis via Intramolecular Ene Reaction. 2. Application to dl-Mesembrine and dl-Dihydromaritidine

The total syntheses of mesembrine (2) and dihydromaritidine (3), alkaloids of the genera Sceletium and Amaryllis (respectively), are decscribed.The key strategy in each case involves the intramolecular ene cyclization of an appropriately constructed acylnitroso olefin, giving cyclic hydroxamic acid ("ene product") 12.Reduction of the hydroxamic acid to the lactam 4 is followed by N-methylation and hydroxylation at position C-6 via bromohydrin 15, introducing the oxygen functionality present in 2.Removal of bromine, oxidation of the alcohol to the keto lactam 13, andreductive removal of the lactam carbonyl gave racemic mesembrine.Removal of bromine from bromohydrin 20, obtained from lactam 4, followed by reduction with lithium aluminum hydride and Pictet-Spengler cyclization gave dihydromaritidine (3).