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- W2067955030 abstract "A diastereodivergent approach for the stereoselective syntheses of all four stereoisomers of galanthamine, (−)-galanthamine 1, (+)-galanthamine 2, (−)-epigalanthamine 3, and (+)-epigalanthamine 4, from (±)-narwedine 5 is reported. Thus (±)-narwedine 5 was resolved by dynamic kinetic resolution to obtain enantiomerically pure (−)-narwedine 6 and (+)-narwedine 7. Each enantiomerically pure isomer of narwedine was subjected to Luche and L-selectride reactions to obtain all four isomers of galanthamine. In these reactions, the (−)-galanthamine 1 and (+)-galanthamine 2 isomers were obtained with an enantiomeric purity of >99.5%, whereas (−)-epigalanthamine 3 and (+)-epigalanthamine 4 are obtained with a chiral purity of >97%. The axial hydride attack by the Luche reduction and the equatorial hydride attack by the L-selectride reduction on the cyclic enone system are explored in the stereoselective synthesis of the galanthamine isomers and thus it was demonstrated that the stereoselective synthesis involving the Luche and L-selectride reductions are complementary in yielding enantiomeric stereogenic centers from a prochiral carbonyl group on the cyclic enone system." @default.
- W2067955030 created "2016-06-24" @default.
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- W2067955030 date "2014-01-01" @default.
- W2067955030 modified "2023-09-25" @default.
- W2067955030 title "Stereoselective syntheses of galanthamine and its stereoisomers by complementary Luche and L-selectride reductions" @default.
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- W2067955030 doi "https://doi.org/10.1016/j.tetasy.2013.11.016" @default.
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