620163-17-9

Upstream product

• 1033702-71-4 C₂₀H₂₃NO₃S 
• 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 
• 646039-38-5 [(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol 
• 646039-39-6 (3R,5R)-5-(4-Methoxy-benzyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol 
• 646039-40-9 (R)-5-(4-Methoxy-benzyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-one 
• 620163-19-1 (2R,4R)-N-[(1-(4-methoxyphenyl)-4-methyl-4,5-epoxy)-pentyl]-4-toluenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 620163-16-8 (2R,4S)-4-hydroxy-2-(4-methoxybenzyl)-4-methyl-1-(4-toluenesulfonyl)pyrrolidine 

Downstream Products

• 128524-63-0 (+)-8-O-methylaphanorphine 

Relevant academic research and scientific papers

An enantioselective approach to (-)-aphanorphine featuring a stereoselective oxidative amidation

A formal enantioselective synthesis of (-)-aphanorphine (91% ee), that culminates with the preparation of (+)-O-methyl aphanorphine, was achieved. The methodology involves the diastereoselective synthesis of a key 3,5-disubstituted pyrrolidinone intermediate by the intramolecular oxidative amidation of a suitably functionalized α-hydroxy pentenoic acid derivative. A late-stage N-formyl protection, which functions as a latent N-methyl group, is utilized as a simple alternative to a protecting group switch and subsequent N-methylation strategy implemented in all other syntheses of aphanorphine related to the present approach. The Royal Society of Chemistry 2013.

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

Enantiocontrolled synthesis of (-)-9-epi-pentazocine and (-)-aphanorphine

(Chemical Equation Presented) We have developed novel asymmetric routes to (-)-9-epi-pentazocine and (-)-aphanorphine from a D-tyrosine derivative. The tricyclic frameworks of (-)-9-epi-pentazocine and (-)-aphanorphine were assembled stereoselectively via intramolecular Friedel-Crafts reaction of the corresponding bicyclic precursors, generated with titanium-promoted enyne cyclization and indium-initiated atom-transfer radical cyclization, respectively.

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

An Efficient Synthesis of (1R,4S)-1-Methyl-8-methoxy-3-(4-toluenesulfonyl)- 2,3,4,5-tetrahydro-1,4-methano-3-benzazepine. A Formal Synthesis of (-)-Aphanorphine

We report a highly efficient synthesis of (1R,4S)-1-methyl-8-methoxy-3-(4- toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine in six steps from 5. The present work constitutes a new formal synthesis of marine alkaloid (-)-aphanorphine.

A facile asymmetric route to (-)-aphanorphine

8O-Methylaphanorphine was synthesized from 4-methoxyphenylacetaldehyde in 36% overall yield and in nine steps, featuring the formation of ring B via a Friedel-Crafts alkylative cyclization with the concomitant stereospecific introduction of the benzylic q