Synthesis of the brominated marine alkaloids (±)-arborescidine A, B and C.

被引：30

作者：

Burm, BEA ^{[1
]}

Meijler, MM ^{[1
]}

Korver, J ^{[1
]}

Wanner, MJ ^{[1
]}

Koomen, GJ ^{[1
]}

机构：

[1] Univ Amsterdam, Organ Chem Lab, Amsterdam Inst Mol Studies, NL-1018 WS Amsterdam, Netherlands

来源：

TETRAHEDRON | 1998年 / 54卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(98)00306-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward synthesis of the brominated marine alkaloids arborescidine A (1), B (2) and C (3), starting from 6-bromo-(N-methyl) trypatamine is described. An equilibrium, under both basic and acidic conditions was found to exist beta een the trans-and cis-isomers 3 and 4. Spectral data indicated that the structure of isomer 4 does not correspond with the compound identified as arborescidine D recently isolated from the marine tunicate Pseudodistoma arborescens. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6135 / 6146

页数：12

共 25 条

[11] 6-BROMOTRYPTAMINE DERIVATIVES FROM THE GULF OF CALIFORNIA TUNICATE DIDEMNUM-CANDIDUM [J].

FAHY, E ;

POTTS, BCM ;

FAULKNER, DJ ;

SMITH, K .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02) :564-569

[12] The pigment of antique magenta from murex brandaris. [J].

Friedlander, P .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1909, 42 :765-770

[13]

GRIBBLE GW, 1972, J ORG CHEM, V37, P9009

[14]

GRON C, 1984, ACTA CHEM SCAND B, V8, P709

[15]

HIRANO S, 1995, HETEROCYCLES, V41, P255

[16]

LARONZE J, 1977, B SOC CHIM FR II-CH, P1195

[17] NONIDENTITY OF NAZLININ AND 6-AZACYCLODECA[5,4-B]INDOL-1-AMINE [J].

MAHBOOBI, S ;

WAGNER, W ;

BURGEMEISTER, T ;

WIEGREBE, W .

ARCHIV DER PHARMAZIE, 1994, 327 (07) :463-465

[18]

MAUPERIN P, 1971, TETRAHEDRON LETT, P999

[19] On the formation of isochinolin-derivatives through the development of methylial on phenyl-aether, phenyl-alanin and tyrosin. [J].

Pictet, A ;

Spengler, T .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1911, 44 :2030-2036

[20] METABOLITES FROM SPONGE PACHYMATISMA-JOHNSTONI - L-6-BROMOHYPAPHORINE, A NEW AMINO-ACID (AND ITS CRYSTAL-STRUCTURE) [J].

RAVERTY, WD ;

THOMSON, RH ;

KING, TJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (10) :1204-1211

← 1 2 3 →