Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides -: chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone

被引：23

作者：

Murahashi, S

Ohtake, H

Imada, Y

机构：

[1] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Osaka 5608531, Japan

[2] Fujisawa Pharmaceut Co Ltd, Basic Res Grp 2, Osaka 5320031, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 18期

关键词：

oxidation; nitrones; asymmetric synthesis; biologically active compounds;

D O I：

10.1016/S0040-4039(98)00333-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)-2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-1-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-1 was also prepared by the oxidation of (S)-2 derived from L-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

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收藏

页码：2765 / 2766

页数：2

相关论文

共 25 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]

Breuer E., 1989, NITRONES NITRONATES, P139

[3] AN ENANTIOSPECIFIC SYNTHESIS OF (+)-RETRONECINE AND RELATED ALKALOIDS [J].

BUCHANAN, JG ;

SINGH, G ;

WIGHTMAN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (19) :1299-1300

[4] 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

[5] NITRONES [J].

DELPIERR.GR ;

LAMCHEN, M .

QUARTERLY REVIEWS, 1965, 19 (04) :329-&

[6] A NITRONE-BASED CYCLOADDITION APPROACH TO THE SYNTHESIS OF THE GLYCOSYL SYSTEM OF NOGALOMYCIN, MENOGARIL, AND THEIR CONGENERS [J].

DESHONG, P ;

LI, W ;

KENNINGTON, JW ;

AMMON, HL ;

LEGINUS, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1364-1373

[7] TOTAL SYNTHESIS OF (+)-RETRONECINE [J].

GEISSMAN, TA ;

WAISS, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) :139-&

[8] STEREOSELECTIVE TOTAL SYNTHESIS OF (+)-LENTIGINOSINE USING A CHIRAL NITRONE INTERMEDIATE [J].

GIOVANNINI, R ;

MARCANTONI, E ;

PETRINI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5706-5707

[9] NITRONES [J].

HAMER, J ;

MACALUSO, A .

CHEMICAL REVIEWS, 1964, 64 (04) :473-+

[10] CYCLOADDITION REACTIONS OF CARBOHYDRATE-DERIVATIVES .4. SYNTHESIS OF A TETRAHYDROXYINDOLIZIDINE THROUGH A CYCLIC NITRONE PREPARED FROM D-XYLOSE [J].

HERCZEGH, P ;

KOVACS, I ;

SZILAGYI, L ;

VARGA, T ;

DINYA, Z ;

SZTARICSKAI, F .

TETRAHEDRON LETTERS, 1993, 34 (07) :1211-1214