Synthetic studies on pentacyclic aromatic alkaloids, kuanoniamine A, 11-hydroxyascididemin, and neocalliactine acetate

被引:27
作者
Kitahara, Y [1 ]
Nakahara, S [1 ]
Yonezawa, T [1 ]
Nagatsu, M [1 ]
Shibano, Y [1 ]
Kubo, A [1 ]
机构
[1] MEIJI COLL PHARM,SETAGAYA KU,TOKYO 154,JAPAN
关键词
D O I
10.1016/S0040-4020(97)10153-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A pentacyclic aromatic alkaloid, kuanoniamine A (6) was synthesized in three steps from 6-methoxybenzothiazole-4,7-dione (8) and 2-aminoacetophenone (9). 11-Hydroxyascididemin (4) was prepared from 5,8-quinolinedione (13, 14) or 1,4-acridinedione (20). The structure of neocalliactine acetate, a derivative of calliactine, was determined to be 5 by total synthesis from 6-methoxy-5,8-quinolinedione (28) and 2-amino-5-methoxyacetophenone (29). (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:17029 / 17038
页数:10
相关论文
共 22 条
[1]   CYSTODAMINE, A NEW CYTOTOXIC FUSED POLYAROMATIC ALKALOID FROM THE MEDITERRANEAN ASCIDIAN CYSTODYTES DELLE CHIAJEI [J].
BONTEMPS, N ;
BONNARD, I ;
BANAIGS, B ;
COMBAUT, G ;
FRANCISCO, C .
TETRAHEDRON LETTERS, 1994, 35 (38) :7023-7026
[2]   POLYCYCLIC AROMATIC ALKALOIDS .2. SYNTHESIS OF ONYCHINE AND EUPOLAURIDINE [J].
BRACHER, F .
ARCHIV DER PHARMAZIE, 1989, 322 (05) :293-294
[3]   SIMPLE AND CONVENIENT DEAMINATION OF AROMATIC-AMINES [J].
CADOGAN, JIG ;
MOLINA, GA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (06) :541-542
[4]   KUANONIAMINE-A, KUANONIAMINE-B, KUANONIAMINE-C, AND KUANONIAMINE-D - PENTACYCLIC ALKALOIDS FROM A TUNICATE AND ITS PROSOBRANCH MOLLUSK PREDATOR CHELYNOTUS-SEMPERI [J].
CARROLL, AR ;
SCHEUER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4426-4431
[5]   STUDIES ON THE STRUCTURE OF CALLIACTINE, THE ZOOCHROME OF THE SEA-ANEMONE CALLIACTIS-PARASITICA [J].
CIMINO, G ;
CRISPINO, A ;
DEROSA, S ;
DESTEFANO, S ;
GAVAGNIN, M ;
SODANO, G .
TETRAHEDRON, 1987, 43 (17) :4023-4030
[6]   SYNTHESIS OF ALKYL-4,7-DIOXOBENZOTHIAZOLES WITH PROPHYLACTIC ANTIMALARIAL ACTIVITY [J].
FRIEDMAN, MD ;
STOTTER, PL ;
PORTER, TH ;
FOLKERS, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (11) :1314-1316
[7]   SYNTHESIS OF ISOASCIDIDEMIN, A REGIOISOMER OF THE MARINE ALKALOID ASCIDIDEMIN [J].
GOMEZBENGOA, E ;
ECHAVARREN, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3497-3501
[8]  
JOOS K, 1978, J CHEM RES M, P4901
[9]  
KITAHARA Y, 1994, HETEROCYCLES, V38, P659
[10]   TOTAL SYNTHESIS OF KUANONIAMINE-A, 11-HYDROXYASCIDIDEMIN, AND NEOCALLIACTINE ACETATE [J].
KITAHARA, Y ;
NAKAHARA, S ;
YONEZAWA, T ;
NAGATSU, M ;
KUBO, A .
HETEROCYCLES, 1993, 36 (05) :943-946