TOTAL SYNTHESIS OF KUANONIAMINE-A, 11-HYDROXYASCIDIDEMIN, AND NEOCALLIACTINE ACETATE

被引：18

作者：

KITAHARA, Y

NAKAHARA, S

YONEZAWA, T

NAGATSU, M

KUBO, A

机构：

[1] Meiji College of Pharmacy, Setagaya-ku, Tokyo, 154

来源：

HETEROCYCLES | 1993年 / 36卷 / 05期

关键词：

D O I：

10.3987/COM-92-6321

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 (5) was synthesized from 6-methoxybenzothiazole-4,7-dione (7) and 2-aminoacetophenone (8). Similarly, 11-hydroxyascididemin (4) was prepared from 6-bromo-4-chloro-5,8-dimethoxyquinoline (12). The structure of neocalliactine acetate, a derivative of calliactine, was determined at 19 by total synthesis from 6-methoxy-5,8-quinolinedione (23) and 2-amino-5-methoxyacetophenone (24).

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页码：943 / 946

页数：4

相关论文

共 19 条

[1] TOTAL SYNTHESIS OF THE PENTACYCLIC ALKALOID ASCIDIDEMIN [J].

BRACHER, F .

HETEROCYCLES, 1989, 29 (11) :2093-2095

[2] 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

[3] DIPLAMINE, A CYTO-TOXIC POLYAROMATIC ALKALOID FROM THE TUNICATE DIPLOSOMA SP [J].

CHARYULU, GA ;

MCKEE, TC ;

IRELAND, CM .

TETRAHEDRON LETTERS, 1989, 30 (32) :4201-4202

[4] 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

[5] THE TOTAL SYNTHESIS OF CYSTODYTINS [J].

CIUFOLINI, MA ;

BYRNE, NE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8016-8024

[6] TOTAL SYNTHESIS OF AMPHIMEDINE [J].

ECHAVARREN, AM ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :4051-4053

[7] 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

[8] SYNTHESIS OF ISOASCIDIDEMIN, A REGIOISOMER OF THE MARINE ALKALOID ASCIDIDEMIN [J].

GOMEZBENGOA, E ;

ECHAVARREN, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3497-3501

[9] 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

[10] CYSTODYTIN-A, CYSTODYTIN-B, AND CYSTODYTIN-C, NOVEL TETRACYCLIC AROMATIC ALKALOIDS WITH POTENT ANTINEOPLASTIC ACTIVITY FROM THE OKINAWAN TUNICATE CYSTODYTES-DELLECHIAJEI [J].

KOBAYASHI, J ;

CHENG, JF ;

WALCHLI, MR ;

NAKAMURA, H ;

HIRATA, Y ;

SASAKI, T ;

OHIZUMI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1800-1804