Synthetic studies on quinine: quinuclidine construction via a ketone enolate regio- and diastereoselective Pd-mediated allylic alkylation |
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Authors: | Johns Deidre M Mori Makoto Williams Robert M |
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Institution: | Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872, USA. |
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Abstract: | 7-Hydroxy-quinine was synthesized by an asymmetric aldol reaction that establishes the C8 and C9 stereochemistry, followed by construction of the 3-vinyl-quinuclidine azabicyclo2.2.2]octane by C3-C4 ring closure using an intramolecular palladium-mediated allylic alkylation with excellent regio- and diastereoselectivity. This is the first report of a ketone-enolate-stereocontrolled allylic alkylation mediated by palladium. The title compound and a dehydro-quinine analogue were evaluated for antimalarial activity. |
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