BROMINE ADDITION TO ALPHA-(1-HYDROXYALKYL)-ALPHA,BETA-UNSATURATED ESTERS AND ALPHA-(1-ALKOXYALKYL)-ALPHA,BETA-UNSATURATED ESTERS - AN APPROACH TO HYDROXYFIMBROLIDE AND BROMOBECKERELIDE

被引：5

作者：

CALDERON, A ^{[1
]}

FONT, J ^{[1
]}

DEMARCH, P ^{[1
]}

机构：

[1] UNIV AUTONOMA BARCELONA,UNITAT QUIM ORGAN,E-08193 BARCELONA,SPAIN

来源：

TETRAHEDRON | 1992年 / 48卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(01)89031-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conventional ionic bromination of electron-poor olefins, 2-(1-hydroxyalkyl)- and 2-(1-alkoxyalkyl)propenoates, 2b-d, and methyl (E)-2-(1-hydroxyethyl)-2-butenoate, 3a, proceeds with yields higher than 80%. Treatment of (E)-3-bromo-2-[1-[(2-methoxyethoxy)methoxy]butyl]propenoic acid, 16, with two equivalents of strong bases, reaction related with a possible hydroxyfimbrolide and bromobeckerelide synthesis, resulted in the halogen-metal exchange reaction affording the acrylic acid 18, presumably through the generation of dianion 19.

引用

页码：5347 / 5358

页数：12

共 37 条

[1] STEREOCHEMISTRY OF THE CONVERSION OF METHACRYLATE TO BETA-HYDROXYISO-BUTYRATE IN PSEUDOMONAS-PUTIDA [J].

ABERHART, DJ ;

TANN, CH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (04) :939-942

[2] NECIC ACID SYNTHONS .2. REGIOSELECTIVITY IN THE REACTIONS OF (Z)-2-BROMOMETHYL-2-ALKENOATE ESTERS WITH SELECTED CARBON NUCLEOPHILES [J].

AMEER, F ;

DREWES, SE ;

EMSLIE, ND ;

KAYE, PT ;

MANN, RL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2293-2295

[3]

Baylis A. B., 1972, CHEM ABSTR 34174Q, V77

[4]

BEECHAN CM, 1979, TETRAHEDRON LETT, P1649

[5] A NEW SYNTHESIS OF 3-NORMAL-BUTYL-4-BROMO-5(Z)-(BROMOMETHYLIDENE)-2-(5H)-FURANONE, A NATURALLY-OCCURRING FIMBROLIDE FROM DELISIA-FIMBRIATA (BONNEMAISONIACEAE) [J].

CAINE, D ;

UKACHUKWU, VC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) :2195-2198

[6]

CAINE D, 1978, TETRAHEDRON LETT, P5167

[7] ACYLATION OF LITHIUM Z-BETA-LITHIOACRYLATES - APPLICATION TO A SHORT SYNTHESIS OF LEPIOCHLORIN [J].

CAINE, D ;

UKACHUKWU, VC .

TETRAHEDRON LETTERS, 1983, 24 (37) :3959-3960

[8] SYNTHESIS OF 3-(1-HYDROXYALKYL)FURAN-2(5H)-ONES - UNEXPECTED SUBSTITUTION-REACTION IN ALLYLIC ALCOHOLS BY BROMINE [J].

CALDERON, A ;

DEMARCH, P ;

FONT, J .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4631-4633

[9]

CANONICA S, 1988, SYNTHESIS-STUTTGART, P697

[10] TRIMETHYL(PHENYL)AMMONIUM PERBROMIDE, AN EFFICIENT REAGENT FOR THE PARTIAL SYNTHESIS OF FUNCTIONALIZED SESQUITERPENE LACTONES [J].

COLLADO, IG ;

MADERO, JG ;

MASSANET, GM ;

LUIS, FR .

TETRAHEDRON LETTERS, 1990, 31 (04) :563-566

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