128524-63-0

Upstream product

• 929872-85-5 C₁₆H₂₁NO₂S₂ 
• 35553-92-5 ETHYL 3-METHOXYPHENYLACETATE 
• 83026-48-6 diethyl (3-methoxyphenyl)methylpropanedioate 
• 178681-63-5 (R)-(+)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene 
• 178681-61-3 (R)-1,2,3,4-tetrahydro-7-methoxy-1-methyl-1-naphthalenemethanol 
• 50874-07-2 2-(3-methoxyphenyl)malonic acid diethyl ester 
• 359882-26-1 (1S,4R)-3-benzyloxycarbonyl-8-methoxy-4-methoxycarbonyl-1-phenylthiomethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 359882-20-5 (1S,9R)-4-Methoxy-1-phenylsulfanylmethyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-9,10-dicarboxylic acid 10-benzyl ester 
• 359882-25-0 (S)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-2-methoxycarbonyl-4-(phenylthiomethylene)pyrrolidine 
• 359882-23-8 (2R,4R)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-2-(methoxycarbonyl)pyrrolidine 
• 359882-24-9 (R)-1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenyl)methyl-2-methoxycarbonyl-4-oxopyrrolidine 
• 620163-16-8 (2R,4S)-4-hydroxy-2-(4-methoxybenzyl)-4-methyl-1-(4-toluenesulfonyl)pyrrolidine 

Downstream Products

• 118964-06-0 (-)-aphanorphine 

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.

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

An effective route to (-)-aphanorphine using D-tyrosine as a chiral building block

A stereoselective approach toward a naturally occurring alkaloid, (-)-aphanorphine, has been achieved via a series of reactions from Boc-D-tyrosine. Georg Thieme Verlag Stuttgart.

Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (-)-aphanorphine

A full account of studies which led to the efficient asymmetric synthesis of (-)-aphanorphine 1 is reported. Two routes to the key cyclic sulfamidate intermediate 5 are described, the first was based on a chiral auxiliary approach and the second utilised

Cyclic sulfamidates as lactam precursors. An efficient asymmetric synthesis of (-)-aphanorphine

A short and efficient enantioselective synthesis of (-)-aphanorphine is described based on the use of a cyclic sulfamidate to provide a suitably functionalised lactam that allows for construction of the tricyclic 3-benzazepine scaffold. The Royal Society

Synthesis of (-)-aphanorphine using a sulfur-directed aryl radical cyclization

Treatment of radical precursor 15a having a vinyl sulfide moiety with Bu3SnH in the presence of AIBN in boiling benzene afforded exclusively the 6-exo cyclization product 16a, whereas similar treatment of the exo-methylene compound 15b gave a mixture of the 6-exo cyclization product 16b and the endo-olefin product 17 formed by a 1,5-hydrogen shift. Based on these findings, the synthesis of (-)-aphanorphine was achieved using a sulfur-directed 6-exo-selective aryl radical cyclization of 22.

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

Synthesis of (-)-aphanorphine using aryl radical cyclization.

[structure: see text] The synthesis of (-)-aphanorphine was achieved by using Bu(3)SnH-mediated aryl radical cyclization of 1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenylmethyl)-2-methoxycarbonyl-4-(phenylthiomethylene)pyrrolidine, leading to exclusive fo

Asymmetric synthesis of benzylic quaternary carbon center via an enzymatic reaction

(R)-(+)- ((R)-(+)-12) and(S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene((S)-(-)-12) were synthesized based on enantioselective PLE hydrolysis of diethyl 2-(m-methoxyphenyl)-2-methylmalonate. From (R)-(+)-12, (+)-O-Methylaphanorphine (16

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.