929641-34-9

Upstream product

• 1301725-81-4 C₂₀H₂₃NO₃ 
• 51-35-4 4R-4-hydroxyproline 
• 98-88-4 benzoyl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 929641-33-8 C₂₀H₂₃NO₃ 
• 444313-68-2 (1R,4R)-N-benzoyl-2-oxa-5-azabicyclo[2.2.1]heptan-3-one 
• 929641-32-7 C₁₉H₁₉NO₃ 
• 947280-04-8 C₁₉H₁₉NO₃ 
• 947280-03-7 C₁₉H₂₁NO₄ 
• 929641-31-6 C₁₉H₂₁NO₃ 
• 929641-30-5 C₂₁H₂₃NO₃S₂ 
• 929641-29-2 C₁₉H₁₉NO₄ 
• 929641-28-1 C₁₄H₁₈N₂O₄ 
• 31560-19-7 (2S,4R)-1-benzoyl-4-hydroxy-L-proline 

Downstream Products

• 126551-98-2 (–)-8-O-methylaphanorphine 

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

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