Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes.

被引：37

作者：

Angelaud, R ^{[1
]}

Landais, Y ^{[1
]}

机构：

[1] UNIV LAUSANNE, COLL PROPEDEUT, INST CHIM ORGAN, CH-1015 LAUSANNE, SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(97)10388-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of pseudo-sugars using the desymmetrization of a dienylsilane, followed by a stereocontrolled introduction of the hydroxymethyl group at C5. is described. The CH2OH group at C5 was elaborated using either a regioselective cyclopropane-ring opening or a [2,3]-Wittig rearrangement. (C) 1997 Elsevier Science Ltd.

引用

页码：8841 / 8844

页数：4

共 27 条

[1] Desymmetrization of a silyl-2,5-cyclohexadiene. Synthesis of (+)-conduritol E and (-)-2-deoxy-allo-inositol [J].

Angelaud, R ;

Landais, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5202-5203

[2] SYNTHESIS OF PSEUDO-ALPHA-L-FUCOPYRANOSE FROM TOLUENE [J].

CARLESS, HAJ ;

MALIK, SS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (23) :2447-2448

[3] REDUCTION OF ARYLTRIMETHYLSILANES AS A SYNTHETIC METHOD .2. BIRCH REDUCTION [J].

EABORN, C ;

JACKSON, RA ;

PEARCE, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (05) :470-474

[4] SYNTHESIS OF PSEUDOSUGARS FROM MICROBIAL METABOLITES [J].

ENTWISTLE, DA ;

HUDLICKY, T .

TETRAHEDRON LETTERS, 1995, 36 (15) :2591-2594

[5] THE MECHANISM OF THE PROTODESILYLATION OF ALLYLSILANES AND VINYLSILANES [J].

FLEMING, I ;

LANGLEY, JA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (05) :1421-1423

[6]

Fleming I., 1989, ORG REACTIONS, V37, P57

[7]

FLEMING I, 1996, CHEMTRACTS ORG CHEM, V9, P1

[8] SILVER-ASSISTED REACTIONS OF ORGANOTIN OXIDES - A MILD, NEUTRAL AND ANHYDROUS ONE-STEP CONVERSION OF PRIMARY ORGANIC HALIDES TO ALCOHOLS [J].

GINGRAS, M ;

CHAN, TH .

TETRAHEDRON LETTERS, 1989, 30 (03) :279-282

[9]

HUTCHINS RO, 1983, J ORG CHEM, V48, P1360, DOI 10.1021/jo00156a045

[10] The oxidation of the carbon-silicon bond [J].

Jones, GR ;

Landais, Y .

TETRAHEDRON, 1996, 52 (22) :7599-7662

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