791780-36-4Relevant academic research and scientific papers
Concise Total Synthesis of (+)-Aphanorphine
Wang, Cheng,Guan, Yukun
supporting information, p. 913 - 916 (2021/04/19)
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
An enantioselective approach to (-)-aphanorphine featuring a stereoselective oxidative amidation
Pansare, Sunil V.,Kulkarni, Kaivalya G.
, p. 19127 - 19134 (2013/10/22)
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
Medjahdi, Mohamed,Gonzalez-Gomez, Jose C.,Foubelo, Francisco,Yus, Miguel
supporting information; experimental part, p. 2230 - 2234 (2011/06/22)
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
Enantioconvergent synthesis of (+)-aphanorphine via asymmetric pd-catalyzed alkene carboamination
Mai, Duy N.,Rosen, Brandon R.,Wolfe, John P.
supporting information; experimental part, p. 2932 - 2935 (2011/07/30)
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
An effective route to (-)-aphanorphine using D-tyrosine as a chiral building block
Li, Min,Zhou, Peijie,Roth, Hans F.
, p. 55 - 60 (2007/12/31)
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.
Further studies on a samarium diiodide-promoted reductive carbon-nitrogen bond cleavage rection: Synthesis of (+)-aphanorphine
Katoh, Miho,Inoue, Hiroshi,Honda, Toshio
, p. 497 - 516 (2008/03/12)
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
Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (-)-aphanorphine
Bower, John F.,Szeto, Peter,Gallagher, Timothy
, p. 143 - 150 (2008/03/28)
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
Formal syntheses of (-)- and (+)-aphanorphine from (2S,4R)-4-hydroxyproline
Ma, Zhiqiang,Hu, Hanwei,Xiong, Wanting,Zhai, Hongbin
, p. 7523 - 7531 (2008/02/08)
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
Ma, Zhiqiang,Zhai, Hongbin
, p. 161 - 163 (2008/03/13)
(-)-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
Enantioselective synthesis of (+)-aphanorphine by means of samarium diiodide promoted reductive carbon-nitrogen bond-cleavage reaction
Katoh, Miho,Inoue, Hiroshi,Suzuki, Atsuko,Honda, Toshio
, p. 2820 - 2822 (2007/10/03)
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
