Efficient and convenient pyridine ring-E formation of the cytotoxic marine alkaloid ascididemin and related analogues.

被引：23

作者：

Lindsay, BS ^{[1
]}

Pearce, AN ^{[1
]}

Copp, BR ^{[1
]}

机构：

[1] UNIV AUCKLAND,DEPT CHEM,AUCKLAND,NEW ZEALAND

来源：

SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 15期

关键词：

D O I：

10.1080/00397919708004128

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conversion of tetracyclic quinone 1 to the cytotoxic pentacyclic alkaloid ascididemin (2) in 80% yield is achieved by reaction with paraformaldehyde and ammonium chloride in refluxing acetic acid. High yielding annelations are also observed for the related analogues N-8 deaza ascididemin (3) and kuanoniamine A (4).

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页码：2587 / 2592

页数：6

相关论文

共 9 条

[1]

BONNARD I, 1995, ANTI-CANCER DRUG DES, V10, P333

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

BRACHER, F .

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

[3] 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

[4] DERCITIN, A NEW BIOLOGICALLY-ACTIVE ACRIDINE ALKALOID FROM A DEEP-WATER MARINE SPONGE, DERCITUS SP [J].

GUNAWARDANA, GP ;

KOHMOTO, S ;

GUNASEKERA, SP ;

MCCONNELL, OJ ;

KOEHN, FE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4856-4858

[5] 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

[6] 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

[7] STRUCTURAL REQUIREMENTS FOR BIOLOGICAL-ACTIVITY OF THE MARINE ALKALOID ASCIDIDEMIN [J].

LINDSAY, BS ;

BARROWS, LR ;

COPP, BR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (07) :739-742

[8] MARINE PYRIDOACRIDINE ALKALOIDS - STRUCTURE, SYNTHESIS, AND BIOLOGICAL CHEMISTRY [J].

MOLINSKI, TF .

CHEMICAL REVIEWS, 1993, 93 (05) :1825-1838

[9] COPYRINE ALKALOIDS - SYNTHESIS, SPECTROSCOPIC CHARACTERIZATION, AND ANTIMYCOTIC - ANTIMYCOBACTERIAL ACTIVITY OF A-RING-FUNCTIONALIZED AND B-RING-FUNCTIONALIZED SAMPANGINES [J].

PETERSON, JR ;

ZJAWIONY, JK ;

LIU, SC ;

HUFFORD, CD ;

CLARK, AM ;

ROGERS, RD .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (22) :4069-4077