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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 21期

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

页码：3257 / 3260

页数：4

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