Unprecedented oxidation of a phenylglycinol-derived 2-pyridone: enantioselective synthesis of polyhydroxypiperidines.
[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.
Amat
M
M
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain. amat@farmacia.far.ub.es
Llor
N
N
Huguet
M
M
Molins
E
E
Espinosa
E
E
Bosch
J
J
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
D004791:Enzyme Inhibitors; D004983:Ethanolamines; D010880:Piperidines; D011728:Pyridones; C005332:N-phenylethanolamine; C017679:2-hydroxypyridine; D006026:Glycoside Hydrolases; D005998:Glycine