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

[1]

ALEMANY A, 1974, B SOC CHIM FR II-CH, P2883

[2]

ANGENOT L, 1975, TETRAHEDRON LETT, P1357

[3] SYNTHESIS OF SOME 5-CHLORO AND 6-CHLORO, 5-METHYL, AND 5,6,7-TRIMETHYL DERIVATIVES OF TRYPTAMINE [J].

BENINGTON, F ;

MORIN, RD ;

CLARK, LC .

JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (09) :1542-1547

[4]

BENSON W, 1981, HETEROCYCLES, V15, P935

[5] (+/-)-GELLIUSINE-A AND (+/-)-GELLIUSINE-B, 2 DIASTEREOMERIC BROMINATED TRIS-INDOLE ALKALOIDS FROM A DEEP-WATER NEW CALEDONIAN MARINE SPONGE (GELLIUS OR ORINA SP) [J].

BIFULCO, G ;

BRUNO, I ;

MINALE, L ;

RICCIO, R ;

CALIGNANO, A ;

DEBITUS, C .

JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1294-1299

[6] SELECTIVE REDUCTIONS .29. A SIMPLE TECHNIQUE TO ACHIEVE AND ENHANCED RATE OF REDUCTION OF REPRESENTATIVE ORGANIC-COMPOUNDS BY BORANE-DIMETHYL SULFIDE [J].

BROWN, HC ;

CHOI, YM ;

NARASIMHAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) :3153-3163

[7] BROMINATED INDOLE ALKALOIDS FROM THE MARINE TUNICATE PSEUDODISTOMA-ARBORESCENS [J].

CHBANI, M ;

PAIS, M ;

DELAUNEUX, JM ;

DEBITUS, C .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (01) :99-104

[8] Enzyme catalysed oxidation of nazlinin and nazlinin derivatives. Characterisation of the reaction products. [J].

Cheng, E ;

Botzem, J ;

Wanner, MJ ;

Burm, BEA ;

Koomen, GJ .

TETRAHEDRON, 1996, 52 (19) :6725-6732

[9] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[10] STRUCTURE AND SYNTHESIS OF A NEW BROMOINDOLE FROM A MARINE SPONGE [J].

DELLAR, G ;

DJURA, P ;

SARGENT, MV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1679-1684

← 1 2 3 →