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15. Efficient Synthesis and Resolution of Pyrrolizidines

R. M. de Figueiredo, R. Fröhlich, M. Christmann

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.

Title
15. Efficient Synthesis and Resolution of Pyrrolizidines
Author
R. M. de Figueiredo, R. Fröhlich, M. Christmann
Identifier
DOI: 10.1002/anie.200605035
Citation
Angew. Chem. Int. Ed. 2007, 46, 2883–2886; (HOT PAPER, highlighted in Synfacts 2007, 795)