A convenient access to (3S)-3-(triisopropylsilyl)oxy-1-pyrroline N-oxide, a useful intermediate for polyfunctionalized enantiopure indolizidine and pyrrolizidine synthesis

被引：53

作者：

Goti, A ^{[1
]}

Cacciarini, M ^{[1
]}

Cardona, F ^{[1
]}

Brandi, A ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, CNR, CSCEA, I-50121 Florence, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 14期

关键词：

nitrones; indolizidines; pyrrolizidines; asymmetric synthesis;

D O I：

10.1016/S0040-4039(99)00310-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optimization of a strategy providing the enantiomerically pure nitrone 2 in five steps and 28% overall yield from L-malic acid has been achieved by the combined use of DIBAL-H as the reductant and triisopropylsilyl as the protecting group. The utility of nitrone 2 as synthetic intermediate is demonstrated by a ready access to polyhydroxylated indolizidines and pyrrolizidines via stereoselective 1,3-dipolar cycloaddition reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2853 / 2856

页数：4

共 33 条

[1] A NITRONE-BASED APPROACH TO THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-ANISOMYCIN [J].

BALLINI, R ;

MARCANTONI, E ;

PETRINI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1316-1318

[2] KINETIC RESOLUTION IN 1,3-DIPOLAR CYCLOADDITION OF TARTARIC ACID-DERIVED NITRONES TO 2,3-DIHYDRO-1-PHENYL-1H-PHOSPHOLES - AN ENANTIOSELECTIVE APPROACH TO THE 2,2'-COUPLED PYRROLIDINE PHOSPHOLANE RING-SYSTEM [J].

BRANDI, A ;

CICCHI, S ;

GOTI, A ;

KOPROWSKI, M ;

PIETRUSIEWICZ, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1315-1318

[3] ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF NATURAL LENTIGINOSINE BY SYNTHESIS AND ENZYMATIC ASSAYS OF OPTICALLY PURE (+)-ENANTIOMERS AND (-)-ENANTIOMERS [J].

BRANDI, A ;

CICCHI, S ;

CORDERO, FM ;

FRIGNOLI, R ;

GOTI, A ;

PICASSO, S ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6806-6812

[4] Straightforward synthesis of (1→2)-linked pseudo aza-C-disaccharides by the novel cycloaddition of enantiopure cyclic nitrones to glycals [J].

Cardona, F ;

Valenza, S ;

Picasso, S ;

Goti, A ;

Brandi, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7311-7318

[5]

Cicchi S, 1998, EUR J ORG CHEM, V1998, P419, DOI 10.1002/(SICI)1099-0690(199803)1998:3<419::AID-EJOC419>3.0.CO

[6]

2-V

[7] NEW SYNTHESIS OF 5-MEMBERED CYCLIC NITRONES FROM TARTARIC ACID [J].

CICCHI, S ;

HOLD, I ;

BRANDI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5274-5275

[8] A 5-MEMBERED ENANTIOPURE CYCLIC NITRONE FROM MALIC-ACID BY REGIOSELECTIVE OXIDATION OF CYCLIC HYDROXYLAMINE - SYNTHESIS OF (1S,7S,8AR)-OCTAHYDRO-1,7-DIHYDROXYINDOLIZINE [J].

CICCHI, S ;

GOTI, A ;

BRANDI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4743-4748

[9] 1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL [J].

CICCHI, S ;

GOTI, A ;

BRANDI, A ;

GUARNA, A ;

DESARLO, F .

TETRAHEDRON LETTERS, 1990, 31 (23) :3351-3354

[10] One step preparation and 1,3-dipolar cycloadditions of (S)-5-hydroxymethyl-1-pyrroline N-oxide [J].

Closa, M ;

deMarch, P ;

Figueredo, M ;

Font, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (07) :1031-1037

← 1 2 3 4 →