Versatile approach to enantiopure 2,6-disubstituted piperidin-3-ol framework: application to the total synthesis of (+)-deoxoprosopinine.
An efficient synthesis of enantiopure 2,6-disubstituted piperidin-3-ol 19 is developed featuring two key steps: (a). Julia olefination of (2R)-3-phenylsulfonyl-2-tert-butyloxycarbamoylpropanol benzyl ether 9B and (2R,3S)-2-tert-butyldiphenyl-3,4-O-isopropylidine-2,3,4-trihydroxybutyraldehyde 8 and (b). intramolecular N-alkylation. A straightforward asymmetric synthesis of (+)-deoxoprosopinine(2) from 19 is described demonstrating the versatility of this novel approach.
Wang
Qian
Q
Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
Sasaki
N André
NA
D000470:Alkaloids / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D010880:Piperidines; C445731:deoxoprosopinine