A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses

被引：24

作者：

Audouard, C ^{[1
]}

Fawcett, J ^{[1
]}

Griffith, GA ^{[1
]}

Kérourédan, E ^{[1
]}

Miah, A ^{[1
]}

Percy, JM ^{[1
]}

Yang, HL ^{[1
]}

机构：

[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 23期

关键词：

D O I：

10.1021/ol0482902

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct precursors to analogues of pentopyranoses, 6-deoxyhexoses, and hexoses, in which a CF2 center replaces the pyranose oxygen, have been synthesized rapidly from trifluoroethanol. A simple scaleable allylation reaction delivers ethers which undergo dehydrofluorination/metalation, followed by addition to either acrolein or cinnamaldehyde, to afford allylic alcohols. Fluorine-assisted [3,3]-rearrangement followed by reduction with sodium borohydride delivers diols, which undergo RCM smoothly to afford cyclohexene diols.

引用

页码：4269 / 4272

页数：4

共 45 条

[1] Ruthenium carbene complexes with imidazol-2-ylidene ligands:: Syntheses of conduritol derivatives reveals superior RCM activity [J].

Ackermann, L ;

El Tom, D ;

Fürstner, A .

TETRAHEDRON, 2000, 56 (15) :2195-2202

[2] The reaction of pyranoside 2-uloses with DAST revised.: Synthesis of 1-fluoro-ketofuranosyl fluorides and their reactivity with alcohols [J].

Aghmiz, ML ;

Díaz, Y ;

Jana, GH ;

Matheu, MI ;

Echarri, R ;

Castillón, S ;

Jimeno, ML .

TETRAHEDRON, 2001, 57 (31) :6733-6743

[3]

AUDOUARD C, UNPUB J FLUORINE CHE

[4] An improved synthesis of 4-O-benzoyl-2,2-difluorooleandrose from L-rhamnose.: Factors determining the synthesis of 2,2-difluorocarbohydrates from 2-uloses [J].

Barrena, MI ;

Matheu, MI ;

Castillón, S .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2184-2188

[5]

BOEHM MF, 1988, TETRAHEDRON LETT, V29, P5217

[6] ACYCLIC STEREOCONTROL INDUCED BY ALLYLIC ALKOXY GROUPS - SYNTHETIC APPLICATIONS OF STEREOSELECTIVE DIHYDROXYLATION IN NATURAL PRODUCT SYNTHESIS [J].

CHA, JK ;

KIM, NS .

CHEMICAL REVIEWS, 1995, 95 (06) :1761-1795

[7] Carbohydrate mimetics-based glycosyltransferase inhibitors [J].

Compain, P ;

Martin, OR .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (12) :3077-3092

[8] Stereloselective synthesis of myo-inositol via ring-closing metathesis:: A building block for glycosylphosphatidylinositol (GPI) anchor synthesis [J].

Conrad, RM ;

Grogan, MJ ;

Bertozzi, CR .

ORGANIC LETTERS, 2002, 4 (08) :1359-1361

[9] Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose [J].

Cox, LR ;

DeBoos, GA ;

Fullbrook, JJ ;

Percy, JM ;

Spencer, NS ;

Tolley, M .

ORGANIC LETTERS, 2003, 5 (03) :337-339

[10]

DAVIS AP, 1996, STEREOSELECTIVE SY E, V21, P3994

← 1 2 3 4 5 →