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Synfacts 2009(8): 0923-0923
DOI: 10.1055/s-0029-1217586
DOI: 10.1055/s-0029-1217586
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
An Organocatalytic Route to Both Enantiomers of Lasubine II
J. M. M. Verkade, F. van der Pijl, M. M. J. H. P. Willems, P. J. L. M. Quaedflieg, F. L. van Delft, F. P. J. T. Rutjes*
Radboud University Nijmegen and DSM Pharmaceutical Products, Geleen, The Netherlands
Further Information
Publication History
Publication Date:
23 July 2009 (online)
Significance
The authors report an enantioselective organocatalytic approach to the total synthesis of lasubine II. Stereochemical information for both of the enantiomers of the natural product was set by using unmodified proline in a three-component Mannich reaction. Subsequent diastereoselective Mannich cyclization afforded the second chiral center, and a Grubbs metathesis followed by functional group manipulation completed the synthesis in a total of ten steps.