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Synfacts 2009(2): 0121-0121  
DOI: 10.1055/s-0028-1087600
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Amurensinine

Contributor(s): Philip Kocienski
D. C. Ebner, R. M. Trend, C. Genet, M. J. McGrath, P. O’Brien*, B. M. Stoltz*
University of York, UK and California Institute of Technology, pasadena, USA
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

An oxidative kinetic resolution procedure using (-)-sparteine˙PdCl2 as a catalyst was previously used by Stoltz and co-workers in a synthesis of the unnatural (+)-amurensinine (J. Am. Chem. Soc. 2006, 128, 11752). (-)-Sparteine, the chiral diamine precursor to complex B, is only commercially available as the (-)-antipode. A ­significant development is the use of O’Brien’s ­diamine G as a surrogate for (+)-sparteine. Diamine G is readily prepared from readily available (-)-cytisine (see: A. J. Dixon, M. J. McGrath, P. O’Brien Org. Synth. 2006, 83, 141).