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Concise Route to (–)‐ and (+)‐Aphanorphine
Author(s) -
Medjahdi Mohamed,
GonzálezGómez José C.,
Foubelo Francisco,
Yus Miguel
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100091
Subject(s) - chemistry , regioselectivity , epoxide , stereoselectivity , alkylation , amine gas treating , derivative (finance) , combinatorial chemistry , friedel–crafts reaction , functional group , organic chemistry , catalysis , polymer , financial economics , economics
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.