SYNTHESIS OF MACROCYCLES VIA ALLYLIC RADICAL INTERMEDIATES - A TOTAL SYNTHESIS OF (-)-ZEARALENONE

被引:54
作者
HITCHCOCK, SA [1 ]
PATTENDEN, G [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)94465-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise synthesis of optically active (-)-zearalenone (1) which uses a novel 14-endo trig macrocyclisation from an allylic radical intermediate (Scheme 1) as a key feature, is described. © 1990.
引用
收藏
页码:3641 / 3644
页数:4
相关论文
共 17 条
[1]   CONVENIENT SYNTHESES OF ALKYL BETA-RESORCYLATE DERIVATIVES [J].
BARRETT, AGM ;
MORRIS, TM ;
BARTON, DHR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (10) :2272-2277
[2]  
Betina V., 1989, CHEM BIOL ENV ASPECT, DOI [10.1016/0300-9629(91)90613-h, DOI 10.1016/0300-9629(91)90613-H]
[3]   RADICAL MACROCYCLIZATIONS IN SYNTHESIS - A NEW APPROACH TO MUKULOL AND MARINE CEMBRANOLIDE LACTONES [J].
COX, NJG ;
PATTENDEN, G ;
MILLS, SD .
TETRAHEDRON LETTERS, 1989, 30 (05) :621-624
[4]   BIOSYNTHESIS OF PARASORBIC ACID (HEX-2-EN-5-OLIDE) BY ROWAN BERRY (SORBUS AUCUPARIA L) [J].
CROMBIE, L ;
FIRTH, PA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (22) :2852-&
[5]  
GIESE B, 1989, TETRAHEDRON LETT, V30, P680
[6]   KNOEVENAGEL CONDENSATION IN HOMOPHTHALIC ACID SERIES - A SYNTHESIS OF ZEARALENONE [J].
GIROTRA, NN ;
WENDLER, NL .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (10) :3192-&
[7]  
HAUSER FM, 1980, SYNTHESIS-STUTTGART, P72
[8]   NOVEL CURVULARIN-TYPE METABOLITES OF A HYBRID STRAIN ME-0005 DERIVED FROM PENICILLIUM CITREO-VIRIDE-B - IFO-6200 AND IFO-4692 [J].
LAI, S ;
SHIZURI, Y ;
YAMAMURA, S ;
KAWAI, K ;
TERADA, Y ;
FURUKAWA, H .
TETRAHEDRON LETTERS, 1989, 30 (17) :2241-2244
[9]   SUGAR-DERIVED CHIRAL BUILDING-BLOCKS .2. SIMPLE SYNTHESIS OF (S)-PARASORBIC ACID AND OTHER (5S)-HYDROXY 6-CARBON SYNTHONS FROM L-RHAMNOSE [J].
LICHTENTHALER, FW ;
KLINGLER, FD ;
JARGLIS, P .
CARBOHYDRATE RESEARCH, 1984, 132 (02) :C1-C4
[10]   NBS BROMINATION SELECTIVITY .6. BROMINATIONS WITH N-BROMOSUCCINIMIDE - SOLVENT AND SELECTIVITY [J].
OFFERMANN, W ;
VOGTLE, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (06) :464-465