TOTAL SYNTHESIS OF (+/-)-MERIDINOL, (+/-)-EPIMERIDINOL, AND A RELATED CYCLOLIGNAN

被引:4
作者
AMER, A [1 ]
BAUER, F [1 ]
ZIMMER, H [1 ]
机构
[1] UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
来源
JOURNAL OF NATURAL PRODUCTS | 1993年 / 56卷 / 04期
关键词
D O I
10.1021/np50094a021
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The naturally occurring lignan meridinol [5] was synthesized in a racemic form in a convergent manner involving a Grignard reaction on E-4-(3,4-methylenedioxybenzylidene)-2,3(2H,5H)-furandione [7]. The hitherto unknown epimeridinol [11] and the cyclolignan 15 were also prepared. The structure assignments of the synthesized lignans are determined by their spectroscopic data.
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页码:600 / 605
页数:6
相关论文
共 13 条
[1]   MERIDINOL, A LIGNAN FROM ZANTHOXYLUM-FAGARA [J].
AMAROLUIS, JM ;
FRONCZEK, FR ;
MASSANET, GM ;
PANDO, E ;
RODRIGUEZLUIS, F ;
WATKINS, SF ;
ZUBIA, E .
PHYTOCHEMISTRY, 1988, 27 (12) :3933-3935
[2]   SUBSTITUTED GAMMA-BUTYROLACTONES .37. SUBSTITUTED GAMMA-LACTONES - REACTIONS OF (ARYLMETHYLENE)FURANDIONES WITH NUCLEOPHILES - A NOVEL-APPROACH TO THE CYCLOLIGNAN LACTONE SKELETON [J].
AMER, A ;
HO, D ;
RUMPEL, K ;
SCHENKEL, RI ;
ZIMMER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5210-5213
[3]   TOTAL SYNTHESIS OF (+/-)-WIKSTROMOL [J].
BELLETIRE, JL ;
FRY, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4724-4729
[4]   EXTRACTIVES OF HELIOPSIS SCABRA - CONSTITUTION OF 2 NEW LIGNANS [J].
BURDEN, RS ;
CROMBIE, L ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (05) :693-&
[5]   PREPARATION OF 2-SUBSTITUTED PODOPHYLLOTOXIN DERIVATIVES [J].
GLINSKI, MB ;
FREED, JC ;
DURST, T .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2749-2753
[6]   KONYANIN - A NEW LIGNAN FROM HAPLOPHYLLUM VULCANICUM [J].
GOZLER, T ;
GOZLER, B ;
PATRA, A ;
LEET, JE ;
FREYER, AJ ;
SHAMMA, M .
TETRAHEDRON, 1984, 40 (07) :1145-1150
[7]  
PALMERSUNGAIL R, 1989, THESIS U CINCINNATI
[8]  
WADA K, 1970, TETRAHEDRON LETT, V27, P2017
[9]   THE SYNTHESIS OF LIGNANS AND NEOLIGNANS [J].
WARD, RS .
CHEMICAL SOCIETY REVIEWS, 1982, 11 (02) :75-125
[10]   LIGNANS AND NEOLIGNANS [J].
WHITING, DA .
NATURAL PRODUCT REPORTS, 1985, 2 (03) :191-211