Thermodynamic equilibration of dihydropyridone enolates: application to the total synthesis of (+/−)-epiuleine |
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Authors: | Edward S. TasberRobert M. Garbaccio |
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Affiliation: | Department of Medicinal Chemistry, Merck Research Laboratories, West Point, PA 19486, USA |
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Abstract: | Following 1,4-reduction of 2-substituted dihydropyridones (1), the requisite ‘kinetic’ enolate can be isomerized upon warming to allow the isolation of the thermodynamic enolate as its vinyl triflate (3). This enolate interconversion is dependent on the dihydropyridone C-2 substituent and can be interpreted in terms of conformational analysis. This novel scaffold (3) opens another avenue for the strategic deployment of dihydropyridones into both natural product synthesis and drug discovery. To this end, this method is highlighted by its use as a key step in a total synthesis of (+/−) epiuleine (14). |
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Keywords: | dihydropyridone tetrahydropyridine enolate epiuleine |
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