MODEL STUDIES TOWARDS A BIOMIMETIC SYNTHESIS OF KERAMAPHIDIN-B AND HALICYCLAMINE-A

被引：25

作者：

GIL, L ^{[1
]}

BAUCHEREL, X ^{[1
]}

MARTIN, MT ^{[1
]}

MARAZANO, C ^{[1
]}

DAS, BC ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 35期

关键词：

D O I：

10.1016/0040-4039(95)01270-R

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As a model for condensation reactions of macrocycles of type 1, which are possibly implicated in the biosynthesis of a number of new alkaloids recently extracted from sponges, we now report that treatment of dihydropyridinium salt 13 with triethylamine in dichloromethane gave, after reduction with sodium borohydride, adducts 15 and 16 in 25% and 7% isolated yields, respectively. The structures of these adducts are identical to the core structures of keramaphidin B, a biogenetic precursor of manzamines, and halicyclamine A

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页码：6231 / 6234

页数：4

相关论文

共 12 条

[1] ON THE BIOSYNTHESIS OF MANZAMINES [J].

BALDWIN, JE ;

WHITEHEAD, RC .

TETRAHEDRON LETTERS, 1992, 33 (15) :2059-2062

[2] A BIOMIMETIC APPROACH TO THE MANZAMINE ALKALOIDS - MODEL STUDIES [J].

BALDWIN, JE ;

CLARIDGE, TDW ;

HEUPEL, FA ;

WHITEHEAD, RC .

TETRAHEDRON LETTERS, 1994, 35 (42) :7829-7832

[3]

CIMINO G, 1986, B SOC CHIM BELG, V95, P783

[4] UNPRECEDENTED ALKALOID SKELETON FROM THE MEDITERRANEAN SPONGE RENIERA-SARAI - X-RAY STRUCTURE OF AN ACETATE DERIVATIVE OF SARAIN-A [J].

CIMINO, G ;

MATTIA, CA ;

MAZZARELLA, L ;

PULITI, R ;

SCOGNAMIGLIO, G ;

SPINELLA, A ;

TRIVELLONE, E .

TETRAHEDRON, 1989, 45 (12) :3863-3872

[5] SYNTHESIS OF MACROCYCLIC OR LINEAR PYRIDINIUM OLIGOMERS FROM 3-SUBSTITUTED PYRIDINES - MODEL SYNTHETIC STUDIES TOWARD MACROCYCLIC MARINE ALKALOIDS [J].

GIL, L ;

GATEAUOLESKER, A ;

WONG, YS ;

CHERNATOVA, L ;

MARAZANO, C ;

DAS, BC .

TETRAHEDRON LETTERS, 1995, 36 (12) :2059-2062

[6] 3-ALKYL 1,6-DIHYDROPYRIDINES FROM 3-ALKYL 5,6-DIHYDRO-PYRIDINIUM SALTS - IMPLICATIONS IN THE BIOSYNTHESIS OF SOME MACROCYCLIC MARINE ALKALOIDS [J].

GIL, L ;

GATEAUOLESKER, A ;

MARAZANO, C ;

DAS, BC .

TETRAHEDRON LETTERS, 1995, 36 (05) :707-710

[7] A TETRACYCLIC DIAMINE ALKALOID, HALICYCLAMINE-A, FROM THE MARINE SPONGE HALICLONA SP [J].

JASPARS, M ;

PASUPATHY, V ;

CREWS, P .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3253-3255

[8] KERAMAPHIDIN-B, A NOVEL PENTACYCLIC ALKALOID FROM A MARINE SPONGE AMPHIMEDON SP - A PLAUSIBLE BIOGENETIC PRECURSOR OF MANZAMINE ALKALOIDS [J].

KOBAYASHI, J ;

TSUDA, M ;

KAWASAKI, N ;

MATSUMOTO, K ;

ADACHI, T .

TETRAHEDRON LETTERS, 1994, 35 (25) :4383-4386

[9] MADANGAMINE-A, A NOVEL CYTOTOXIC ALKALOID FROM THE MARINE SPONGE XESTOSPONGIA-INGENS [J].

KONG, FM ;

ANDERSEN, RJ ;

ALLEN, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6007-6008

[10] INGENAMINE, A NOVEL PENTACYCLIC ALKALOID FROM THE MARINE SPONGE XESTOSPONGIA INGENS [J].

KONG, FM ;

ANDERSEN, RJ ;

ALLEN, TM .

TETRAHEDRON LETTERS, 1994, 35 (11) :1643-1646