An Organocatalytic Route to Both Enantiomers of Lasubine
II

doi:10.1055/s-0029-1217586

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Synfacts 2009(8): 0923-0923
DOI: 10.1055/s-0029-1217586

Organo- and Biocatalysis

An Organocatalytic Route to Both Enantiomers of Lasubine II

Contributor(s): Benjamin List, Olga Lifchits
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

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Publikationsverlauf

Publikationsdatum:
23. Juli 2009 (online)

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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.