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

被引:42
作者
Amat, M [1 ]
Llor, N
Huguet, M
Molins, E
Espinosa, E
Bosch, J
机构
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
[2] Inst Ciencia Mat, CSIC, Cerdanyola Del Valles, Spain
关键词
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.
引用
收藏
页码:3257 / 3260
页数:4
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