1301725-76-7Relevant articles and documents
Concise route to (-)- and (+)-aphanorphine
Medjahdi, Mohamed,Gonzalez-Gomez, Jose C.,Foubelo, Francisco,Yus, Miguel
, 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