TOTAL SYNTHESIS OF PLAGIOCHIN-C AND PLAGIOCHIN-D, MACROCYCLIC BIS(BIBENZYL) CONSTITUENTS OF PLAGIOCHILA-ACANTOPHYLLA

被引:33
作者
KESERU, GM
MEZEYVANDOR, G
NOGRADI, M
VERMES, B
KAJTARPEREDY, M
机构
[1] HUNGARIAN ACAD SCI,ALKALOID CHEM RES GRP,POB 91,H-1521 BUDAPEST,HUNGARY
[2] HUNGARIAN ACAD SCI,CENT RES INST CHEM,H-1525 BUDAPEST,HUNGARY
关键词
PLAGIOCHINS; BIS(BIBENZYLS); SYNTHESIS; MACROCYCLES; WURTZ REACTION;
D O I
10.1016/S0040-4020(01)88193-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Plagiochins C (3) and D (4) were synthesized by convergent schemes. Rings C and B were joined by Ullman ether synthesis, the aryl-aryl bond between rings A and D was formed by Pd(0)-catalysed coupling of an arylboronic acid (ring D) and a bromobenzoic ester (ring A). Ring C and D were linked by the Wittig reaction, while final ring closure was effected by tetraphenylethene assisted Wurtz reaction.
引用
收藏
页码:913 / 922
页数:10
相关论文
共 15 条
[1]   SYNTHESIS OF [2.2]METACYCLOPHANES [J].
BOEKELHE.V ;
GRIFFIN, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1960-+
[2]  
CHRISTENSEN BG, 1983, Patent No. 4374849
[3]  
DAVIES H, 1928, J CHEM SOC, P605
[4]  
DIENES Z, 1989, LIEBIGS ANN CHEM, P1141
[5]   TOTAL SYNTHESES OF RICCARDIN-A, RICCARDIN-B, AND RICCARDIN-C, CYTOTOXIC MACROCYCLIC BIS(BIBENZYLS) FROM LIVERWORTS [J].
GOTTSEGEN, A ;
NOGRADI, M ;
VERMES, B ;
KAJTARPEREDY, M ;
BIHATSIKARSAI, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02) :315-320
[6]  
GRONOWITZ S, 1984, CHEM SCRIPTA, V24, P5
[7]  
HA NT, 1991, J CHEM RES M, P1240
[8]  
HA NTT, 1991, J CHEM RES-S, P137
[9]   PLAGIOCHIN-A, PLAGIOCHIN-B, PLAGIOCHIN-C, AND PLAGIOCHIN-D, NEW TYPE OF MACROCYCLIC BIS(BIBENZYLS) HAVING A BIPHENYL LINKAGE BETWEEN THE ORTHO-POSITIONS TO THE BENZYL METHYLENES, FROM THE LIVERWORT PLAGIOCHILA-ACANTHOPHYLLA SUBSP JAPONICA [J].
HASHIMOTO, T ;
TORI, M ;
ASAKAWA, Y ;
FUKAZAWA, Y .
TETRAHEDRON LETTERS, 1987, 28 (50) :6295-6298
[10]  
HODGSON HH, 1926, J CHEM SOC, V127, P876