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

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Stereoselective synthesis of pyridinones: application to the synthesis of (-)-barrenazines.

[reaction: see text] The stereoselective synthesis of pyridinones was accomplished by the nucleophilic addition of Grignard reagents to a chiral pyridinium salt derived from 4-methoxypyridine. This methodology was applied to an expedient synthesis of (-)-barrenazine A and B. After N-functionalization and 1,4-reduction of the pyridinone system, the corresponding alpha-amino piperidinones readily undergo dimerization to give the hexahydrodipyridinopyrazine skeleton of the barrenazine alkaloids.[1]

References

  1. Stereoselective synthesis of pyridinones: application to the synthesis of (-)-barrenazines. Focken, T., Charette, A.B. Org. Lett. (2006) [Pubmed]
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