SYNTHESIS OF 5-ALKYL-4-BROMO-5-HYDROXY-2(5H)-FURANONES AND 5-ALKYLIDENE-4-BROMO-2(5H)-FURANONES

被引:13
作者
FONT, J
GRACIA, A
DEMARCH, P
机构
[1] Unitat de Química Orgánica. Universitat Autònoma de Barcelona.
关键词
D O I
10.1016/S0040-4039(00)97887-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of monoalkylsubstituted allenic esters 4 with NBS and water in the darkness yields β-bromo-γ,β-butenolides 5, that are easily transformed into 5-alkyl-4-bromo-5-hydroxy-2(5H)-furanones 8 and 5-alkylidene-4-bromo-2(5H)-furanones 2. © 1990.
引用
收藏
页码:5517 / 5520
页数:4
相关论文
共 22 条
[1]  
BEECHAN CM, 1979, TETRAHEDRON LETT, P1649
[2]   ETHYLIDENETETRONIC ACID AND ITS DERIVATIVES - CONDENSATIONS WITH CARBONYL-COMPOUNDS, LEADING TO REASSIGNMENT OF RAMIGENIC ACID FROM PENICILLIUM-CHARLESII [J].
BEGLEY, MJ ;
CLEMO, NG ;
PATTENDEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2393-2397
[3]   DIRECTED METALLATIONS OF 4-ETHYLIDENETETRONIC ACID O-METHYL ETHER AND ITS DERIVATIVES AS A SYNTHETIC ENTRY TO NATURAL 4-OXYFURAN-2-ONES [J].
BUCK, J ;
CLEMO, NG ;
PATTENDEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2399-2405
[4]   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
[5]   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
[6]   SYNTHESIS OF (E)-PULVINONES AND (Z)-PULVINONES [J].
CAMPBELL, AC ;
MAIDMENT, MS ;
PICK, JH ;
STEVENSON, DFM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08) :1567-1576
[7]  
FONT J, 1983, MERCK INDEX, P1137
[8]  
FONT J, IN PRESS TETRAHEDRON
[9]  
FONT J, 1989, AN QUIM C, V85
[10]   REACTIVITY OF ALPHA-HALOBUTYROLACTONES WITH TERTIARY HALOGENS IN THE PRESENCE OF WEAKLY BASIC NUCLEOPHILES [J].
GHARBIBENAROUS, J ;
ESSAYEGH, MM ;
DANA, G .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09) :2031-2038