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

共 38 条

[31] Nash R.J., 1996, ALKALOIDS CHEM BIOL, V11, P345, DOI DOI 10.1016/S0735-8210(96)80009-4
[32] Nishimura Y., 1995, STUD NAT PROD CHEM, V16, P75
[33] NEW POTENT ALPHA-GLUCOHYDROLASE INHIBITOR MDL-73945 WITH LONG DURATION OF ACTION IN RATS
ROBINSON, KM
BEGOVIC, ME
RHINEHART, BL
HEINEKE, EW
DUCEP, JB
KASTNER, PR
MARSHALL, FN
DANZIN, C
[J]. DIABETES, 1991, 40 (07) : 825 - 830
[34] Conformationally restricted analogues of methionine: Synthesis of chiral 3-amino-5-methylthio-2-piperidones
Rodriguez, R
Estiarte, MA
Diez, A
Rubiralta, M
Colell, A
GarciaRuiz, C
FernandezCheca, JC
[J]. TETRAHEDRON, 1996, 52 (22) : 7727 - 7736
[35] SCHWESINGER R, 1996, STEREOSELECTIVE SYNT, V8, P4599
[36] Stutz A.E., 1999, IMINOSUGARS GLYCOSID
[37] 6-0-BUTANOYLCASTANOSPERMINE (MDL 28,574) INHIBITS GLYCOPROTEIN PROCESSING AND THE GROWTH OF HIV
TAYLOR, DL
SUNKARA, PS
LIU, PS
KANG, MS
BOWLIN, TL
TYMS, AS
[J]. AIDS, 1991, 5 (06) : 693 - 698
[38] 1986, DRUGS FUTURE, V11, P1039

← 1 2 3 4 →