Premium
Enantioselective Total Synthesis of (+)‐Homochelidonine by a Pd II ‐Catalyzed Asymmetric Ring‐Opening Reaction of a meso ‐Azabicyclic Alkene with an Aryl Boronic Acid
Author(s) -
McManus Helen A.,
Fleming Matthew J.,
Lautens Mark
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200603945
Subject(s) - enantioselective synthesis , alkene , chemistry , ring (chemistry) , boronic acid , aryl , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , alkyl
An efficient and highly convergent enantioselective synthesis of (+)‐homochelidonine has been achieved (see scheme; Cbz=benzyloxycarbonyl, MOM=methoxymethyl) and relied on a new and powerful desymmetrizing ring‐opening reaction of a meso ‐azabicycle with an aryl boronic acid. The route should allow access to other hexahydrobenzo[ c ]phenanthridine alkaloids.