Stereoselective synthesis of [3.3.0]-fused γ-butyrolactones of carbohydrates

被引：9

作者：

Alibés, R

Bourdelande, JL

Gregori, A

Font, J ^{[1
]}

Rustullet, A

Parella, T

机构：

[1] Univ Autonoma Barcelona, Unitat Quim Organ, Dept Quim, Bellaterra 08193, Barcelona, Spain

[2] Univ Autonoma Barcelona, Servei Ressonancia Magnet Nucl, Bellaterra 08193, Barcelona, Spain

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2003年 / 22卷 / 7-8期

关键词：

cyclobutanes; stereoselection; fused gamma-butyrolactones; lyxofuranose;

D O I：

10.1081/CAR-120026454

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A facile and stereoselective method is described for the preparation of fused 2,3-gamma-butyrolactones of lyxofuranose from the unexpected rearrangement in basic media of the photocycloadduct between homochiral 2(5H)-furanones and vinylene carbonate.

引用

收藏

页码：501 / 511

页数：11

相关论文

共 15 条

[1] STEREOSELECTIVE (2+2) PHOTOCYCLOADDITION OF CHIRAL 2(5H)-FURANONES TO ALKENES [J].

ALIBES, R ;

BOURDELANDE, JL ;

FONT, J .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1391-1402

[2] Stereoselective [2+2] photocycloaddition of acetylene to chiral 2(5H)-furanones [J].

Alibés, R ;

de March, P ;

Figueredo, M ;

Font, J ;

Racamonde, M .

TETRAHEDRON LETTERS, 2001, 42 (38) :6695-6697

[3] [2+2] Photocycloaddition of homochiral 2(5H)-furanones to alkenes. First step for an efficient and diastereoselective synthesis of (+)- and (-)-grandisol [J].

Alibes, R ;

Bourdelande, JL ;

Font, J ;

Gregori, A ;

Parella, T .

TETRAHEDRON, 1996, 52 (04) :1267-1278

[4] SYNTHESIS OF HOMOCHIRAL TRISUBSTITUTED GAMMA-BUTYROLACTONES [J].

ALKER, D ;

JONES, DN ;

TAYLOR, GM ;

WOOD, WW .

TETRAHEDRON LETTERS, 1991, 32 (13) :1667-1670

[5]

BACH T, 1989, SYNTHESIS-STUTTGART, P145

[6] ALKYLATION OF (1S,2R,5R,6S,7R)- AND (1R,2R,5R,6S,7S)-5-METHYL-4-OXATRICYCLO-[5.2.1.0/2,6]-8-DECEN-3-ONE - APPLICATION TO THE SYNTHESIS OF (R)-3-ALKYL-5-METHYL-2(5H)-FURANONES [J].

CORBERA, J ;

FONT, J ;

MONSALVATJE, M ;

ORTUNO, RM ;

SANCHEZFERRANDO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4393-4395

[7] Highly diastereoselective [2+2] photocycloaddition of homochiral 2(5H)-furanones to vinylene carbonate [J].

Gregori, A ;

Alibés, R ;

Bourdelande, JL ;

Font, J .

TETRAHEDRON LETTERS, 1998, 39 (38) :6961-6962

[8] Facile and stereoselective synthesis of fused γ-butyrolactones of carbohydrates [J].

Gregori, A ;

Alibés, R ;

Bourdelande, JL ;

Font, J .

TETRAHEDRON LETTERS, 1998, 39 (38) :6963-6966

[9] Synthesis, structure and reactions of uridine 2'-C,3'-O-gamma-butyrolactone: versatile intermediate for the synthesis of 2'-C-branched nucleosides [J].

Lawrence, AJ ;

Pavey, JBJ ;

Chan, MY ;

Fairhurst, RA ;

Collingwood, SP ;

Fisher, J ;

Cosstick, R ;

ONeil, IA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (18) :2761-2767

[10] Diastereoselective synthesis of α-substituted-γ-butyrolactones of nucleosides via [1,5]-C,H insertion reactions of α-diazomalonates of nucleosides [J].

Lim, J ;

Choo, DJ ;

Kim, YH .

CHEMICAL COMMUNICATIONS, 2000, (07) :553-554