TOTAL SYNTHESIS OF THE MYCOTOXIN (-)-ZEARALENONE BASED ON MACROCYCLIZATION USING A CINNAMYL RADICAL INTERMEDIATE

被引:25
作者
HITCHCOCK, SA [1 ]
PATTENDEN, G [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 11期
关键词
D O I
10.1039/p19920001323
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, which uses a novel 14-endo-trig macrocyclisation from a cinnamyl radical intermediate onto an alpha, beta-enone electrophore as a key feature, is described.
引用
收藏
页码:1323 / 1328
页数:6
相关论文
共 30 条
[1]   THE ISOLATION, IDENTIFICATION, AND BIOASSAY OF THE ANTIFUNGAL METABOLITES PRODUCED BY MONOCILLIUM-NORDINII [J].
AYER, WA ;
LEE, SP ;
TSUNEDA, A ;
HIRATSUKA, Y .
CANADIAN JOURNAL OF MICROBIOLOGY, 1980, 26 (07) :766-773
[2]   TRIS(TRIMETHYLSILYL)SILANE AS A RADICAL-BASED REDUCING AGENT IN SYNTHESIS [J].
BALLESTRI, M ;
CHATGILIALOGLU, C ;
CLARK, KB ;
GRILLER, D ;
GIESE, B ;
KOPPING, B .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :678-683
[3]   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
[4]  
Betina V., 1989, CHEM BIOL ENV ASPECT, DOI [10.1016/0300-9629(91)90613-h, DOI 10.1016/0300-9629(91)90613-H]
[5]  
BETINA V, 1984, MYCOTOXINS PRODUCTIO
[6]  
BOECKMAN RK, 1973, TOTAL SYNTHESIS NATU, V7, P1
[7]  
COX NJ, 1992, J CHEM SOC P1
[8]   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
[9]   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-&
[10]   TRIS(TRIMETHYLSILYL)SILANE AS MEDIATOR IN ORGANIC-SYNTHESIS VIA RADICALS [J].
GIESE, B ;
KOPPING, B ;
CHATGILIALOGLU, C .
TETRAHEDRON LETTERS, 1989, 30 (06) :681-684