FREE RADICAL-INDUCED C-ALLYLATION OF ALPHA-BROMOLACTONES - SYNTHESIS OF 2-C-ALLYL-2-DEOXY-D-ARABINONO-1,4-LACTONE AND 2-C-ALLYL-2-DEOXY-D-RIBONO-1,4-LACTONE

被引：7

作者：

HANESSIAN, S

LEGER, R

ALPEGIANI, M

机构：

[1] Department of Chemistry, Université de Montréal, Succ. A. Montrel, Que. H3C 3J7

来源：

CARBOHYDRATE RESEARCH | 1992年 / 228卷 / 01期

关键词：

D O I：

10.1016/S0008-6215(00)90556-1

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：

Application of the Keck C-allylation of organic halides to 2-bromo-2-deoxy-D-arabinonolactone resulted in the formation of mixtures of 2-C-allyl lactones. The stereochemical preferences observed were dictated by the nature of vicinal and remotely placed substituents in the lactone.

引用

页码：145 / 155

页数：11

共 73 条

[1] APPLICATIONS OF RADICAL-ADDITION REACTIONS TO THE SYNTHESIS OF A C-GLUCOSIDE AND A FUNCTIONALIZED AMINO-ACID
ADLINGTON, RM
BALDWIN, JE
BASAK, A
KOZYROD, RP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) : 944 - 945
[2] SYNTHESIS OF C-GLYCOSYL COMPOUNDS BY THE ADDITION OF GLYCOSYL RADICALS TO OLEFINS
ARAKI, Y
ENDO, T
TANJI, M
NAGASAWA, J
ISHIDO, Y
[J]. TETRAHEDRON LETTERS, 1987, 28 (47) : 5853 - 5856
[3] RADICAL CYCLIZATION ON CARBOHYDRATE PYRANOSIDES - A CONTROLLED FORMATION OF FUNCTIONALIZED RING-FUSED BICYCLIC ACETALS
AUDIN, C
LANCELIN, JM
BEAU, JM
[J]. TETRAHEDRON LETTERS, 1988, 29 (30) : 3691 - 3694
[4] OXYGEN CARBON BETA-BOND EFFECTS IN RADICAL REACTIONS
BARTON, DHR
HARTWIG, W
MOTHERWELL, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (08) : 447 - 448
[5] STEREOELECTRONIC EFFECTS IN HYDROGEN-ATOM ABSTRACTION FROM SUBSTITUTED 1,3-DIOXANES
BECKWITH, ALJ
EASTON, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) : 615 - 619
[6] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS
BECKWITH, ALJ
[J]. TETRAHEDRON, 1981, 37 (18) : 3073 - 3100
[7] DIRECT BUTYROLACTONE PRODUCTION USING TIN HYDRIDE
BELLETIRE, JL
MAHMOODI, NO
[J]. TETRAHEDRON LETTERS, 1989, 30 (33) : 4363 - 4366
[8] REACTION OF ALDONIC ACIDS WITH HYDROGEN BROMIDE .3. THE PREPARATION OF SOME BROMODEOXY-PENTONOLACTONES AND DIBROMODIDEOXY-PENTONOLACTONES
BOCK, K
LUNDT, I
PEDERSEN, C
[J]. CARBOHYDRATE RESEARCH, 1981, 90 (01) : 17 - 26
[9] THE STEREOCHEMISTRY OF THE STORK SILYL METHYLENE RADICAL CYCLIZATION IN AN ANNULATED SUGAR DERIVATIVE
BONNERT, RV
DAVIES, MJ
HOWARTH, J
JENKINS, PR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (02) : 148 - 149
[10] STEREOSELECTIVE METHYLATION OF BETA-HYDROXYLACTONE DIANIONS
CHAMBERLIN, AR
DEZUBE, M
[J]. TETRAHEDRON LETTERS, 1982, 23 (30) : 3055 - 3058

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