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An Asymmetric Approach towards (–)‐Aphanorphine and Its Analogues
Author(s) -
Donets Pavel A.,
Goeman Jan L.,
Van der Eycken Johan,
Robeyns Koen,
Van Meervelt Luc,
Van der Eycken Erik V.
Publication year - 2009
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.200801175
Subject(s) - chemistry , enantioselective synthesis , intramolecular force , alkaloid , stereochemistry , ring (chemistry) , total synthesis , tricyclic , benzazepine , radical cyclization , organic chemistry , catalysis
A short enantioselective approach towards the alkaloid(–)‐aphanorphine and its substituted analogues is described. The enantiomerically pure starting material for the synthesis was obtained by asymmetric hydrogenation in the presence of the Rh–( S )‐PipPhos complex. Microwave‐assisted Heckcyclization selectively provided the seven‐membered 3‐benzazepine ring. Further, the assembly of the tricyclic core of the alkaloid was accomplished by intramolecular radical cyclization. The X‐ray structure confirming the absolute configuration of the obtained products is described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)