Synthesis of didemnolines A-D, N9-substituted β-carboline alkaloids from the marine ascidian Didemnum sp.

被引：46

作者：

Schumacher, RW

Davidson, BS ^{[1
]}

机构：

[1] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA

[2] Utah State Univ, Dept Chem & Biochem, Logan, UT 84322 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 04期

关键词：

natural products; alkaloids; imidazoles;

D O I：

10.1016/S0040-4020(98)01100-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Didemnolines A-D (1-4) were synthesized and their structures were confirmed through comparisons of data for the synthetic material with those obtained for natural 1-4. The synthesis of didemnolines A (1) and C (3) involved the coupling of l-[(benzyloxy)methyl]-4-chloromethyl-5-(thiomethyl)imidazole (6) with 7-bromo-beta-carboline (5), while didemnolines B (2) and D (4) were formed through the analogous coupling of 6 with norharmon (7). Intermediate 6 was efficiently prepared from 1-[(benzyloxy)methyl]-2,4,5-tribromoimidazole using a sequential one-pot halogen-metal exchange reaction and 7-Br-beta-carboline was synthesized using a new approach (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：935 / 942

页数：8

相关论文

共 31 条

[1] SYNTHESIS OF CAMALEXIN AND RELATED PHYTOALEXINS [J].

AYER, WA ;

CRAW, PA ;

MA, YT ;

MIAO, SC .

TETRAHEDRON, 1992, 48 (14) :2919-2924

[2] THE STEREOCHEMISTRY OF EUDISTOMIN-C, EUDISTOMIN-K, EUDISTOMIN-E, EUDISTOMIN-F AND EUDISTOMIN-L [J].

BLUNT, JW ;

LAKE, RJ ;

MUNRO, MHG ;

TOYOKUNI, T .

TETRAHEDRON LETTERS, 1987, 28 (16) :1825-1826

[3] ASCIDIANS - PRODUCERS OF AMINO-ACID DERIVED METABOLITES [J].

DAVIDSON, BS .

CHEMICAL REVIEWS, 1993, 93 (05) :1771-1791

[4] ALKALOIDS OF A NEW-CALEDONIAN SEA-SQUIRT, EUDISTOMA-FRAGUM [J].

DEBITUS, C ;

LAURENT, D ;

PAIS, M .

JOURNAL OF NATURAL PRODUCTS, 1988, 51 (04) :799-801

[5] Bengacarboline, a new beta-carboline from a marine ascidian Didemnum sp. [J].

Foderaro, TA ;

Barrows, LR ;

Lassota, P ;

Ireland, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6064-6065

[6] MULTIFUNCTIONALIZATION OF IMIDAZOLE VIA SEQUENTIAL HALOGEN-METAL EXCHANGE - A NEW ROUTE TO PURINE-RING ANALOGS [J].

GROZIAK, MP ;

WEI, LL .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3776-3780

[7] REGIOSELECTIVE FORMATION OF IMIDAZOL-2-YLLITHIUM, IMIDAZOL-4-YLLITHIUM, AND IMIDAZOL-5-YLLITHIUM SPECIES [J].

GROZIAK, MP ;

WEI, LL .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4296-4300

[8]

HO BT, 1988, ORG SYNTH COLL VOL, V6, P965

[9] AZOLES .6. A CONVENIENT SYNTHESIS OF POLYSUBSTITUTED IMIDAZOLES FROM 1-PROTECTED 2,4,5-TRIBROMOIMIDAZOLES [J].

IDDON, B ;

KHAN, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (07) :1453-1455

[10] AZOLES .11. SYNTHESIS OF IMIDAZOLE-2-CARBALDEHYDE AND IMIDAZOLE-5-CARBALDEHYDE AND DERIVATIVES OF IMIDAZO[1,2-B]ISOQNINOLINE - TRANSMETALATION OF IMIDAZOL-5-YLLITHIUM COMPOUNDS [J].

IDDON, B ;

PETERSEN, AK ;

BECHER, J ;

CHRISTENSEN, NJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12) :1475-1481

← 1 2 3 4 →