Polycyclic aromatic alkaloids .11. A convenient formal total synthesis of the cytotoxic marine alkaloid amphimedine

被引:0
作者
Bracher, F
Papke, T
机构
来源
LIEBIGS ANNALEN | 1996年 / 01期
关键词
amphimedine; alkaloid; palladium catalyst; cross coupling; anellation;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The pyridylbenzo[c][2,7]naphthyridinone 2, a central intermediate for the total synthesis of amphimedine (1), was prepared in two steps from the readily available quinoline 3. Palladium-catalyzed cross-coupling of 3 with 4-(trimethylstannyl)pyridine gave the biarene 4, which could be converted to the target compound 2 by using a one-pot anellation method.
引用
收藏
页码:115 / 116
页数:2
相关论文
共 11 条
[1]   POLYCYCLIC AROMATIC ALKALOIDS .3. SYNTHESIS OF PERLOLIDINE [J].
BRACHER, F .
ARCHIV DER PHARMAZIE, 1989, 322 (08) :511-512
[2]   POLYCYCLIC AROMATIC ALKALOIDS .10. ANNONACEOUS ALKALOIDS WITH ANTIFUNGAL ACTIVITY [J].
BRACHER, F .
ARCHIV DER PHARMAZIE, 1994, 327 (06) :371-375
[3]  
Camps R., 1902, ARCH PHARM, V240, P135, DOI 10.1002/ardp.19022400204
[4]   TOTAL SYNTHESIS OF AMPHIMEDINE [J].
ECHAVARREN, AM ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :4051-4053
[5]   AN ORIGINAL ONE-POT SYNTHESIS OF 5-(4-PYRIDYL)-BENZO[C]-2,7-NAPHTHYRIDINE AS KEY INTERMEDIATE IN THE SYNTHESIS OF AMPHIMEDINE BY METALATION CONNECTED WITH CROSS-COUPLING REACTION [J].
GUILLIER, F ;
NIVOLIERS, F ;
GODARD, A ;
MARSAIS, F ;
QUEGUINER, G .
TETRAHEDRON LETTERS, 1994, 35 (35) :6489-6492
[6]   COMBINE METALATION PALLADIUM-CATALYZED CROSS-COUPLING STRATEGIES - A FORMAL SYNTHESIS OF THE MARINE ALKALOID AMPHIMEDINE [J].
GUILLIER, F ;
NIVOLIERS, F ;
GODARD, A ;
MARSAIS, F ;
QUEGUINER, G ;
SIDDIQUI, MA ;
SNIECKUS, V .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) :292-296
[7]   SYNTHESIS OF AMPHIMEDINE, A NEW FUSED AROMATIC ALKALOID FROM A PACIFIC SPONGE, AMPHIMEDON SP [J].
KUBO, A ;
NAKAHARA, S .
HETEROCYCLES, 1988, 27 (09) :2095-2098
[8]   CALYCANTHINE .5. ON CALYCANINE [J].
MARION, L ;
MANSKE, RHF ;
KULKA, M .
CANADIAN JOURNAL OF RESEARCH SECTION B-CHEMICAL SCIENCES, 1946, 24 (05) :224-231
[9]   BONDING IN TRIORGANOTIN PYRIDINES [J].
PHILLIPS, JE ;
HERBER, RH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 268 (01) :39-47
[10]   A SIMPLE SYNTHESIS OF AMPHIMEDINE [J].
PRAGER, RH ;
TSOPELAS, C ;
HEISLER, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (02) :277-285