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Unprecedented oxidation of a phenylglycinol-derived 2-pyridone: Enantioselective synthesis of polyhydroxypiperidines
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作者:

Amat, M
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Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

Llor, N
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Huguet, M
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Molins, E
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Espinosa, E
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机构: Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

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[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
[2] Inst Ciencia Mat, CSIC, Cerdanyola Del Valles, Spain
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D O I:
10.1021/ol016418z
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
[GRAPHICS] 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-dihydroxyplperidlne is also reported.
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页码:3257 / 3260
页数:4
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