A convenient new route to 4-substituted benzo[de][3,6]phenanthrolin-6(6H)-ones:: Important intermediates in the synthesis of ring-A analogues of the cytotoxic marine alkaloid ascididemin.

被引:10
作者
Copp, BR [1 ]
Hansen, RP [1 ]
Appleton, DR [1 ]
Lindsay, BS [1 ]
Squire, CJ [1 ]
Clark, GR [1 ]
Rickard, CEF [1 ]
机构
[1] Univ Auckland, Dept Chem, Auckland, New Zealand
关键词
D O I
10.1080/00397919908086428
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-ethylthio- and 4-(4 "-methylphenylthio)benzo[de][3,6]phenanthrolin-6(6H)-one have been synthesised in 4 steps from benzoquinone and then readily converted to the 4-amino (6d) and 4-methoxy (6c) analogues by nucleophilic substitution. Further elaboration of 6d leads to the synthesis of 11-hydroxyascididemin, which we have found to exhibit antiviral activity in vitro.
引用
收藏
页码:2665 / 2676
页数:12
相关论文
共 11 条
[1]  
ALCALAY W, 1947, HELV CHIM ACTA, V15, P579
[2]  
BAKER LJ, 1998, IN PRESS ACTA CRYST
[3]   TOTAL SYNTHESIS OF THE PENTACYCLIC ALKALOID ASCIDIDEMIN [J].
BRACHER, F .
HETEROCYCLES, 1989, 29 (11) :2093-2095
[4]   BIOMIMETIC SYNTHESIS OF PYRIDO[2,3,4-KL]ACRIDINES [J].
GELLERMAN, G ;
RUDI, A ;
KASHMAN, Y .
TETRAHEDRON LETTERS, 1993, 34 (11) :1823-1826
[5]   USE OF SULFOXIDES AS COCATALYSTS IN THE PALLADIUM QUINONE-CATALYZED 1,4-DIACETOXYLATION OF 1,3-DIENES - AN EXAMPLE OF LIGAND-ACCELERATED CATALYSIS [J].
GRENNBERG, H ;
GOGOLL, A ;
BACKVALL, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5808-5811
[6]   Synthetic studies on pentacyclic aromatic alkaloids, kuanoniamine A, 11-hydroxyascididemin, and neocalliactine acetate [J].
Kitahara, Y ;
Nakahara, S ;
Yonezawa, T ;
Nagatsu, M ;
Shibano, Y ;
Kubo, A .
TETRAHEDRON, 1997, 53 (50) :17029-17038
[7]   ASCIDIDEMIN, A NOVEL PENTACYCLIC AROMATIC ALKALOID WITH POTENT ANTILEUKEMIC ACTIVITY FROM THE OKINAWAN TUNICATE DIDEMNUM SP [J].
KOBAYASHI, J ;
CHENG, JF ;
NAKAMURA, H ;
OHIZUMI, Y ;
HIRATA, Y ;
SASAKI, T ;
OHTA, T ;
NOZOE, S .
TETRAHEDRON LETTERS, 1988, 29 (10) :1177-1180
[8]   Efficient and convenient pyridine ring-E formation of the cytotoxic marine alkaloid ascididemin and related analogues. [J].
Lindsay, BS ;
Pearce, AN ;
Copp, BR .
SYNTHETIC COMMUNICATIONS, 1997, 27 (15) :2587-2592
[9]  
PRATT YT, 1962, J CHEM SOC, P3905
[10]   CYTOTOXIC AROMATIC ALKALOIDS FROM THE ASCIDIAN AMPHICARPA-MERIDIANA AND LEPTOCLINIDES SP - MERIDINE AND 11-HYDROXYASCIDIDEMIN [J].
SCHMITZ, FJ ;
DEGUZMAN, FS ;
HOSSAIN, MB ;
VANDERHELM, D .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :804-808