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Efficient Synthesis and Resolution of Pyrrolizidines
Author(s) -
de Figueiredo Renata Marcia,
Fröhlich Roland,
Christmann Mathias
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.200605035
Subject(s) - enantiomer , maleimide , enantioselective synthesis , pyrrolizidine , resolution (logic) , chemistry , stereochemistry , kinetic resolution , combinatorial chemistry , chromatography , computer science , organic chemistry , programming language , catalysis
In only two steps the commercially available maleimide 1 is converted into the key pyrrolizidine carboxylic acid unit ( 2 ) of the telomerase inhibitor UCS1025A. A kinetic resolution through an enantioselective oxa‐Michael lactonization and trituration of the resulting scalemic mixture allow for a virtually quantitative separation of a racemate into the enantiomers.