Enantioselective Total Synthesis of (+)‐Homochelidonine by a Pd II ‐Catalyzed Asymmetric Ring‐Opening Reaction of a  meso ‐Azabicyclic Alkene with an Aryl Boronic Acid | Zendy

McManus Helen A. | Zendy; Fleming Matthew J. | Zendy; Lautens Mark | Zendy

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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.

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