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Synthesis of (-)-Amurensinine
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
22 January 2009 (online)
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).