THE SYNTHESIS OF PLICATIN-B VIA THE HECK REACTION

被引:17
作者
BATES, RW
GABEL, CJ
机构
[1] Department of Chemistry, University of North Texas, Denton, TX 76203
关键词
D O I
10.1016/S0040-4039(00)73632-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The anti-microbial natural product Plicatin B has been synthesized in 53% overall yield using a Heck reaction as the key step. The optimum conditions for this reaction have been determined. Halophenols proved much less reactive than their corresponding acetates.
引用
收藏
页码:3547 / 3550
页数:4
相关论文
共 10 条
[1]   NATURALLY OCCURRING TERPENE DERIVATIVES .196. NEW DITERPENE AND OTHER COMPOUNDS FROM BACCHARIS SPECIES [J].
BOHLMANN, F ;
KNAUF, W ;
KING, RM ;
ROBINSON, H .
PHYTOCHEMISTRY, 1979, 18 (06) :1011-1014
[2]   SYNTHESIS OF 6-SUBSTITUTED-3,4-DIHYDRO-2H-1-BENZOPYRAN-2-ONES(DIHYDROCOUMARINS) VIA PALLADIUM CATALYZED COUPLING REACTIONS [J].
DAVIES, SG ;
PYATT, D ;
THOMSON, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 387 (03) :381-390
[3]   A CONVENIENT SOLVENT-SPECIFIC SYNTHESIS OF 4-[4-ACETOXY-3-(3-METHYLBUT-2-ENYL)PHENYL]BUTYRIC ACID [J].
FATOPE, MO ;
OKOGUN, JI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (07) :1601-1603
[4]  
GERRARD W, 1957, P CHEM SOC LONDON, P19
[5]  
Heck R. F., 1985, PALLADIUM REAGENTS O, P276
[6]  
MOLYNEUX R J, 1970, Tetrahedron, V26, P4743, DOI 10.1016/S0040-4020(01)93125-4
[7]   PLICATIN-A AND PLICATIN-B 2 PHENOLIC CINNAMATES FROM PSORALEA-PLICATA [J].
RASOOL, N ;
KHAN, AQ ;
MALIK, A .
PHYTOCHEMISTRY, 1990, 29 (12) :3979-3981
[8]   PLICATIN-B, THE ANTIMICROBIAL PRINCIPLE OF PSORALEA-JUNCEA [J].
SCHMITT, A ;
TELIKEPALLI, H ;
MITSCHER, LA .
PHYTOCHEMISTRY, 1991, 30 (11) :3569-3570
[9]  
SHARMA DN, 1984, TETRAHEDRON LETT, V25, P5581
[10]   PALLADIUM-CATALYZED VINYLIC SUBSTITUTION WITH HIGHLY ACTIVATED ARYL HALIDES [J].
ZIEGLER, CB ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :2941-2946