Stylissadines A and B:: The first tetrameric pyrrole-imidazole alkaloids

被引:69
作者
Grube, Achim [1 ]
Koeck, Matthias [1 ]
机构
[1] Alfred Wegener Inst Polar & Meeresforsh Helmholtz, D-27570 Bremerhaven, Germany
关键词
D O I
10.1021/ol061317s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrrole - imidazole alkaloids are widely distributed in marine sponges of the orders Halichondrida and Agelasida. Chemical investigation of the Caribbean sponge Stylissa caribica led to the isolation of the first tetrameric pyrrole - imidazole alkaloids. The so-called stylissadines are the largest and most complex pyrrole - imidazole alkaloids discovered so far and are therefore a major challenge for the structure determination by NMR spectroscopy. Their isolation and structure elucidation are discussed in detail.
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收藏
页码:4675 / 4678
页数:4
相关论文
共 12 条
[1]  
Al Mourabit A, 2001, EUR J ORG CHEM, V2001, P237
[2]   CHEMOTAXONOMY OF AGELAS (PORIFERA, DEMOSPONGIAE) [J].
BRAEKMAN, JC ;
DALOZE, D ;
STOLLER, C ;
VANSOEST, RWM .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1992, 20 (05) :417-431
[3]   Marine natural products [J].
Faulkner, DJ .
NATURAL PRODUCT REPORTS, 2002, 19 (01) :1-48
[4]   NEW BROMO-PYRROLE DERIVATIVES FROM SPONGE AGELAS-OROIDES [J].
FORENZA, S ;
MINALE, L ;
RICCIO, R .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (18) :1129-&
[5]   REINVESTIGATION INTO STRUCTURE OF OROIDIN, A BROMOPYRROLE DERIVATIVE FROM MARINE SPONGE [J].
GARCIA, EE ;
BENJAMIN, LE ;
FRYER, RI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (03) :78-79
[6]   Isolation and synthesis of 4-bromopyrrole-2-carboxyarginine and 4-bromopyrrole-2-carboxy-N(ε)-lysine from the marine sponge Stylissa caribica [J].
Grube, A ;
Lichte, E ;
Köck, M .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (01) :125-127
[7]   Oxocyclostylidol, an intramolecular cyclized oroidin derivative from the marine sponge Stylissa caribica [J].
Grube, Achim ;
Koeck, Matthias .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (08) :1212-1214
[8]   Synthesis of the pyrrole-imidazole alkaloids [J].
Hoffmann, H ;
Lindel, T .
SYNTHESIS-STUTTGART, 2003, (12) :1753-1783
[9]   Challenge palau'amine: Current standings [J].
Jacquot, DEN ;
Lindel, T .
CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) :1551-1565
[10]   BIOACTIVE BROMOPYRROLE METABOLITES FROM THE CARIBBEAN SPONGE AGELAS-CONIFERA [J].
KEIFER, PA ;
SCHWARTZ, RE ;
KOKER, MES ;
HUGHES, RG ;
RITTSCHOF, D ;
RINEHART, KL .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2965-2975