126551-98-2

Upstream product

• 126552-38-3 (2S,4S)-6-Methoxy-4-methyl-4-methylaminomethyl-1,2,3,4-tetrahydro-naphthalen-2-ol 
• 50-00-0 formaldehyd 
• 51-35-4 4R-4-hydroxyproline 
• 1301725-81-4 C₂₀H₂₃NO₃ 
• 1308799-03-2 (+/-)-tert-butyl (2-hydroxy-2-methylpent-4-en-1-yl)carbamate 
• 1308799-00-9 (+/-)-tert-butyl {2-methyl-2-[(trimethylsilyl)oxy]pent-4-en-1-yl}carbamate 
• 1308799-02-1 (+)-(2S)-tert-butyl 2-(4-methoxybenzyl)-4-methyl-4-[(trimethylsilyl)oxy]pyrrolidine-1-carboxylate 
• 1308799-06-5 (+)-(5S)-5-(4-methoxybenzyl)-3-methyl-1-tosylpyrrolidin-3-ol 
• 1308799-08-7 (+)-(1S,4S)-8-methoxy-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-1,4-methanobenzo[d]azepine 
• 83287-29-0 (3S,5R)-5-Hydroxymethyl-3-(3-methoxy-phenyl)-3-methyl-dihydro-furan-2-one 
• 943920-30-7 (4S)-4-(tert-butyldimethylsiloxymethyl)-8-methoxy-1,3-dimethyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one 
• 943920-32-9 methanesulfonic acid 7-methoxy-3,5-dimethyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[d]azepin-2-ylmethyl ester 

Downstream Products

• 126640-92-4 (+)-aphanorphine 

Relevant academic research and scientific papers

Concise route to (-)- and (+)-aphanorphine

This paper presents an application of two recently developed methodologies to the synthesis of naturally occurring (-)-aphanorphine. The first method involves an indium-mediated stereoselective α-aminoallylation of aldehydes to prepare enantioenriched homoallylic amine derivatives. The second is the epoxidation and regioselective opening of the epoxide to afford 2-substituted 3-pyrrolidinols. The synthesis was completed by using a reported Friedel-Crafts alkylation and conventional functional-group manipulation. According to the same route, the O-methyl derivative of unnatural (+)-aphanorphine was prepared from (S)-2-methylpropane-2-sulfinamide. A straightforward synthesis of the marine alkaloid (-)-aphanorphine was accomplished in 9 steps from commercially available starting materials. Indium-mediated stereoselective α-aminoallylation of an aldehyde, pyrrolidin-3-ol formation byintramolecular nucleophilic opening of an epoxide, and intramolecular Friedel-Crafts alkylation are the key steps in this synthesis. Through this methodology, natural (-)-aphanorphine and its enantiomer are affordable. Copyright

Enantioselective synthesis of (+)-aphanorphine by means of samarium diiodide promoted reductive carbon-nitrogen bond-cleavage reaction

An enantioselective synthesis of (+)-aphanorphine has been achieved by application of a samarium diiodide promoted reductive carbon-nitrogen bond-cleavage reaction to a 1-methoxy-carbonyl-1,2,3,4-tetrahydroisoquinoline providing a benzazepinone derivative

Concise Total Synthesis of (+)-Aphanorphine

A concise total synthesis of (+)-aphanorphine is described. The key features of the strategy include a Pd-catalyzed intermolecular trimethylenemethane [3+2]-cycloaddition to form ring C and a Co-catalyzed radical cyclization through a hydrogen-atom transf

Enantiocontrolled Synthesis of (+)-Aphanorphine from (R)-O-Benzylglycidol: Assignment of Absolute Configuration

Aphanorphine, a novel 3-benzazepine alkaloid isolated from the freshwater blue-green alga Aphanizomenon flos-aquae, has been syntesized in the antipodal forms starting from (R)-O-benzylglycidol to establish the absolute configuration of the natural produc

Enantioconvergent synthesis of (+)-aphanorphine via asymmetric pd-catalyzed alkene carboamination

A concise asymmetric synthesis of (+)-aphanorphine has been achieved via a new enantioconvergent strategy. A racemic γ-aminoalkene derivative is transformed into a 1:1 mixture of enantiomerically enriched diastereomers using an asymmetric Pd-catalyzed car

Formal syntheses of (-)- and (+)-aphanorphine from (2S,4R)-4-hydroxyproline

We describe the efficient formal syntheses of both natural (-)-aphanorphine and unnatural (+)-aphanorphine from the same commercially available amino acid, (2S,4R)-4-hydroxyproline. The tricyclic framework was constructed by intramolecular Friedel-Crafts

A concise formal synthesis of unnatural (+)-aphanorphine from (2S,4R)-4-hydroxyproline

(-)-Aphanorphine methyl ether was synthesized in ten steps from commercially available (2S,4R)-4-hydroxyproline, featuring the C-2 configuration inversion of an intermediate amide and intramolecular Friedel-Crafts reaction. The present work constitutes a

Further studies on a samarium diiodide-promoted reductive carbon-nitrogen bond cleavage rection: Synthesis of (+)-aphanorphine

Samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was applied to the 1,2,3,4-tetrahydroisoquinoline derivatives bearing an ester group at the 1- or 3-position to give the corresponding benzazepinones. Synthesis of (+)-aphanorphine was esta

ASYMMETRIC SYNTHESES OF O-METHYLAPHANORPHINE

Two routes leading to the preparation of racemic, (+), and (-) O-methylaphanorphine via the asymmetric alkylation of 2-oxazolines are described.