SAMARIUM(II) IODIDE PROMOTED RING CONTRACTION OF CARBOHYDRATE-DERIVATIVES - AN EXPEDITIOUS SYNTHESIS OF FUNCTIONALIZED CYCLOPENTANES

被引：35

作者：

CHENEDE, A ^{[1
]}

POTHIER, P ^{[1
]}

SOLLOGOUB, M ^{[1
]}

FAIRBANKS, AJ ^{[1
]}

SINAY, P ^{[1
]}

机构：

[1] ECOLE NORMALE SUPER,CNRS,DEPT CHEM,F-75231 PARIS 05,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 13期

关键词：

D O I：

10.1039/c39950001373

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aldehydo methyl pyranosides undergo ring contraction induced by treatment with samarium(ii) iodide, in the presence of HMPA and tert-butyl alcohol, to give highly functionalised cyclopentanes.

引用

页码：1373 / 1374

页数：2

共 26 条

[1] RULES FOR RING-CLOSURE - APPLICATION TO INTRAMOLECULAR ALDOL CONDENSATIONS IN POLYKETONIC SUBSTRATES [J].

BALDWIN, JE ;

LUSCH, MJ .

TETRAHEDRON, 1982, 38 (19) :2939-2947

[2] SYNTHESIS OF 6-DEOXY-D-MANNO-HEPTOSE [J].

BOREN, HB ;

EKLIND, K ;

GAREGG, PJ ;

LINDBERG, B ;

PILOTTI, A .

ACTA CHEMICA SCANDINAVICA, 1972, 26 (10) :4143-4146

[3] ASYMMETRIC CYCLOPROPANATION OF ALLYLIC ETHERS - CLEAVAGE AND REGENERATION OF THE CHIRAL AUXILIARY [J].

CHARETTE, AB ;

COTE, B .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :933-936

[4]

CURRAN DP, 1992, SYNLETT, P943

[5] TETRAHYDROPYRAN RING-OPENING REACTIONS PROMOTED BY SMI2 [J].

ENHOLM, EJ ;

SCHREIER, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1110-1111

[6] UNSATURATED CARBOHYDRATES .21. CARBOCYCLIC RING-CLOSURE OF A HEX-5-ENOPYRANOSIDE DERIVATIVE [J].

FERRIER, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1455-1458

[7] THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES [J].

FERRIER, RJ ;

MIDDLETON, S .

CHEMICAL REVIEWS, 1993, 93 (08) :2779-2831

[8] SAMARIUM DIIODIDE-MEDIATED DEOXYGENATION OF TAXOL - A ONE-STEP SYNTHESIS OF 10-DEACETOXYTAXOL [J].

GEORG, GI ;

CHERUVALLATH, ZS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :4015-4018

[9]

HANESSIAN S, 1994, SYNLETT, P863

[10] A PRACTICAL SYNTHESIS OF 2-DEOXY ALDONOLACTONES VIA A SMI2-MEDIATED ALPHA-DEOXYGENATION REACTION [J].

HANESSIAN, S ;

GIRARD, C ;

CHIARA, JL .

TETRAHEDRON LETTERS, 1992, 33 (05) :573-576

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