Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from D-ribose

被引：17

作者：

Argyropoulos, NG ^{[1
]}

Panagiotidis, TD ^{[1
]}

Gallos, JK ^{[1
]}

机构：

[1] Aristotle Univ Thessaloniki, Dept Chem, Thessaloniki 54124, Greece

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 05期

关键词：

D O I：

10.1016/j.tetasy.2006.02.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：829 / 836

页数：8

共 60 条

[31] Synthesis of enantiopure 3-substituted pyrroline N-oxides by highly regioselective oxidation of the parent hydroxylamines: A mechanistic rationale [J].

Goti, A ;

Cicchi, S ;

Fedi, V ;

Nannelli, L ;

Brandi, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3119-3125

[32] (1S,2S,7R,8aS)- and (1S,2S,7S,8aS)-trihydroxyoctahydroindolizine: Two new glycosidase inhibitors by nitrone cycloaddition strategy [J].

Goti, A ;

Cardona, F ;

Brandi, A ;

Picasso, S ;

Vogel, P .

TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1659-1674

[33]

Goti A, 1997, SYNLETT, P577

[34] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .31. GENERATION OF NITRONES FROM OXIMES - BACKGROUND AND SCOPE OF THE TANDEM 1,2-PROTOTROPY-INTRAMOLECULAR CYCLOADDITION SEQUENCE [J].

GRIGG, R ;

HEANEY, F ;

MARKANDU, J ;

SURENDRAKUMAR, S ;

THORNTONPETT, M ;

WARNOCK, WJ .

TETRAHEDRON, 1991, 47 (24) :4007-4030

[35] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .37. GENERATION OF NITRONES FROM OXIMES - TANDEM INTRAMOLECULAR 1,3-AZAPROTIO CYCLOTRANSFER INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS - CLASS-4 PROCESSES [J].

GRIGG, R ;

MARKANDU, J ;

SURENDRAKUMAR, S ;

THORNTONPETT, M ;

WARNOCK, WJ .

TETRAHEDRON, 1992, 48 (47) :10399-10422

[36] X=Y - ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .35. GENERATION OF NITRONES FROM OXIMES - CLASS-3 PROCESSES - TANDEM INTRAMOLECULAR MICHAEL ADDITION (1,3-AZAPROTIO CYCLOTRANSFER) - INTERMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS [J].

GRIGG, R ;

MARKANDU, J ;

PERRIOR, T ;

SURENDRAKUMAR, S ;

WARNOCK, WJ .

TETRAHEDRON, 1992, 48 (33) :6929-6952

[37]

GRUNANGER P, 1994, CHEM HETEROCYCL COMP, V49, P649

[38]

Hall A, 1997, SYNLETT, P123

[39]

Holzapfel CW, 1998, HETEROCYCLES, V48, P1337

[40] MICROBIAL OXIDATION OF CHLOROAROMATICS IN THE ENANTIODIVERGENT SYNTHESIS OF PYRROLIZIDINE ALKALOIDS - TRIHYDROXYHELIOTRIDANES [J].

HUDLICKY, T ;

LUNA, H ;

PRICE, JD ;

RULIN, F .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4683-4687

← 1 2 3 4 5 6 →