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
BALDWIN, JE
LUSCH, MJ
[J]. TETRAHEDRON, 1982, 38 (19) : 2939 - 2947
[2] SYNTHESIS OF 6-DEOXY-D-MANNO-HEPTOSE
BOREN, HB
EKLIND, K
GAREGG, PJ
LINDBERG, B
PILOTTI, A
[J]. ACTA CHEMICA SCANDINAVICA, 1972, 26 (10): : 4143 - 4146
[3] ASYMMETRIC CYCLOPROPANATION OF ALLYLIC ETHERS - CLEAVAGE AND REGENERATION OF THE CHIRAL AUXILIARY
CHARETTE, AB
COTE, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) : 933 - 936
[4] CURRAN DP, 1992, SYNLETT, P943
[5] TETRAHYDROPYRAN RING-OPENING REACTIONS PROMOTED BY SMI2
ENHOLM, EJ
SCHREIER, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) : 1110 - 1111
[6] UNSATURATED CARBOHYDRATES .21. CARBOCYCLIC RING-CLOSURE OF A HEX-5-ENOPYRANOSIDE DERIVATIVE
FERRIER, RJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06): : 1455 - 1458
[7] THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES
FERRIER, RJ
MIDDLETON, S
[J]. CHEMICAL REVIEWS, 1993, 93 (08) : 2779 - 2831
[8] SAMARIUM DIIODIDE-MEDIATED DEOXYGENATION OF TAXOL - A ONE-STEP SYNTHESIS OF 10-DEACETOXYTAXOL
GEORG, GI
CHERUVALLATH, ZS
[J]. 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
HANESSIAN, S
GIRARD, C
CHIARA, JL
[J]. TETRAHEDRON LETTERS, 1992, 33 (05) : 573 - 576

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