General Au-Catalyzed Benzannulation Towards Naturally Occurring Carbazole Alkaloids from Methoxypropadiene

被引：68

作者：

Kong, Wangqing ^{[1
]}

Fu, Chunling ^{[1
]}

Ma, Shengming ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 47期

基金：

中国国家自然科学基金;

关键词：

alkaloids; annulation; carbazoles; methoxypropadienes; natural products; synthetic methods; COMBRETASTATIN A-4 ANALOGS; TRANSITION-METAL-COMPLEXES; 1ST TOTAL-SYNTHESIS; ORGANIC-SYNTHESIS; COUPLING REACTION; HIGHLY EFFICIENT; N-DEBENZYLATION; PALLADIUM; HETEROCYCLES; CHEMISTRY;

D O I：

10.1002/chem.201102251

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Accessible alkaloids: Naturally occurring carbazole alkaloids, such as clauszoline-K, -L, -M, and -N, 3-formyl-7-hydroxycarbazole, and siamenol, were synthesized through a gold-catalyzed cyclization reaction of 1-(indol-2-yl)-2-methoxy-2,3-allenols, which are readily available from indolecarbaldehydes and methoxypropadiene (see scheme; R 1=Me, carboxylic acid/ester, or aldehyde; R 2=prenyl or H; R 3=H or Me). The reaction demonstrates atom economy, high selectivity, and high yields, mostly with catalytic reactions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：13134 / 13137

页数：4

共 46 条

[1] CATALYTIC OXIDATIVE AROMATIC CYCLIZATIONS WITH PALLADIUM [J].

AKERMARK, B ;

OSLOB, JD ;

HEUSCHERT, U .

TETRAHEDRON LETTERS, 1995, 36 (08) :1325-1326

[2]

AKERMARK B, 1975, J ORG CHEM, V40, P1365, DOI 10.1021/jo00897a048

[3] SYNTHESIS OF CARBAZOLE ALKALOIDS [J].

BERGMAN, J ;

PELCMAN, B .

PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1967-1976

[4]

BERNARD AM, 1989, SYNTHESIS-STUTTGART, P287

[5]

Brandsma L., 1981, SYNTHESIS ACETYLENES

[6] Sugars, Alkaloids, and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes [J].

Brasholz, Malte ;

Reissig, Hans-Ulrich ;

Zimmer, Reinhold .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (01) :45-56

[7] RECENT ADVANCES IN THE CHEMISTRY OF CARBAZOLE [J].

CAMPBELL, N ;

BARCLAY, BM .

CHEMICAL REVIEWS, 1947, 40 (03) :359-380

[8] Demand-based thiolate anion generation under virtually neutral conditions: Influence of steric and electronic factors on chemo- and regioselective cleavage of aryl alkyl ethers [J].

Chakraborti, AK ;

Sharma, L ;

Nayak, MK .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) :6406-6414

[9]

Chakraborty D. P., 1977, PROGR CHEM ORGANIC N, V34, P299

[10] ON CONSTITUTION OF MURRAYANINE A CARBAZOLE DERIVATIVE ISOLATED FROM MURRAYA KOENIGII SPRENG [J].

CHAKRABORTY, DP ;

BARMAN, BK ;

BOSE, PK .

TETRAHEDRON, 1965, 21 (03) :681-+

← 1 2 3 4 5 →