Stereoselective synthesis of pyridinones: application to the synthesis of (-)-barrenazines |
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Authors: | Focken Thilo Charette André B |
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Institution: | Department of Chemistry, Université de Montréal, Station Downtown, Quebec, Canada. |
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Abstract: | 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. |
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