title: Unprecedented oxidation of a phenylglycinol-derived 2-pyridone: enantioselective synthesis of polyhydroxypiperidines.
abstract: [reaction: see text]. The phenylglycinol-derived 2-pyridone 1 undergoes m-CPBA oxidation steroselectively leading to the chiral nonracemic unsaturated bicyclic hydroxylactam 2, from which the enantioselective synthesis of (3R,5R)-3,4,5-trihydroxypiperidine (16) and the formal synthesis of the azasugar epiisofagomine are described. The enantioselective synthesis of (S)-N-Boc-3-hydroxypiperidine and (3R,4S)-3,4-dihydroxypiperidine is also reported.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain. amat@farmacia.far.ub.es
authors.forename: M
authors.initials: M
authors.lastname: Amat
authors.forename: N
authors.initials: N
authors.lastname: Llor
authors.forename: M
authors.initials: M
authors.lastname: Huguet
authors.forename: E
authors.initials: E
authors.lastname: Molins
authors.forename: E
authors.initials: E
authors.lastname: Espinosa
authors.forename: J
authors.initials: J
authors.lastname: Bosch
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis*; D011728:Pyridones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004791:Enzyme Inhibitors; D004983:Ethanolamines; D010880:Piperidines; D011728:Pyridones; C005332:N-phenylethanolamine; C017679:2-hydroxypyridine; D006026:Glycoside Hydrolases; D005998:Glycine