1301725-71-2

Upstream product

• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 196929-78-9 (R)-2-methylpropane-2-sulfinamide 

Downstream Products

• 1301725-73-4 (2R)-N-(tert-butylsulfonyl)-1-(4-methoxyphenyl)-3-(2-methyloxiran-2-yl)propan-2-ylamine 
• 1301725-75-6 (5R)-N-(tert-butylsulfonyl)-5-(4-methoxybenzyl)-3-methylpyrrolidin-3-ol 
• 1301725-76-7 (5R)-N-(benzoyl)-5-(4-methoxybenzyl)-3-methylpyrrol-idin-3-ol 
• 1301725-78-9 (1R,4R)-N-benzoyl-8-methoxy-1-methyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 118964-06-0 (-)-aphanorphine 
• 128524-63-0 (+)-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