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Catalytic Enantioselective Total Synthesis of Hodgkinsine B
Author(s) -
Snell Robert H.,
Woodward Robert L.,
Willis Michael C.
Publication year - 2011
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.201103864
Subject(s) - enantioselective synthesis , oxindole , palladium , total synthesis , catalysis , chemistry , absolute configuration , stereochemistry , organic chemistry , combinatorial chemistry
The power of palladium : The total synthesis of the alkaloid hodgkinsine B has been achieved with just six isolated intermediates and only four chromatographic operations. The route involves a palladium‐catalyzed enantioselective desymmetrizing N‐allylation of meso ‐ chimonanthine to establish the absolute configuration and elaboration of the desymmetrized core by a diastereoselective palladium‐catalyzed α‐oxindole arylation.