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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Total synthesis of (-)-senepodine G and (-)-cermizine C.

An efficient, stereospecific synthesis of the alkaloids senepodine G (2) and cermizine C (1) has been completed using the BF3.Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3, the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).[1]


  1. Total synthesis of (-)-senepodine G and (-)-cermizine C. Snider, B.B., Grabowski, J.F. J. Org. Chem. (2007) [Pubmed]
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