Total Synthesis of (±)-Communesin F via a Cycloaddition with Indol-2-one

被引：98

作者：

Belmar, Johannes ^{[1
]}

Funk, Raymond L. ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 41期

基金：

美国国家卫生研究院;

关键词：

COMMUNESINS; PEROPHORAMIDINE; NOMOFUNGIN; ALKALOIDS;

D O I：

10.1021/ja307277w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise total synthesis of (+/-)-communesin F has been completed in 15 linear steps from 4-bromotryptophol in an overall yield of 6.7%. A key step features the cycloaddition of indol-2-one with 3-(2-azidoethyl)-4-bromoindole and facilitates the rapid construction of the lower aminal-containing tetracyclic core of the natural product.

引用

页码：16941 / 16943

页数：3

共 29 条

[1]

Abel-Magid A. F., 2006, ORG PROCESS RES DEV, V10, P971

[2] An approach to the total synthesis of the marine ascidian metabolite perophoramidine via a halogen-selective tandem Heck/carbonylation strategy [J].

Artman, GD ;

Weinreb, SM .

ORGANIC LETTERS, 2003, 5 (09) :1523-1526

[3]

BASHA A, 1977, TETRAHEDRON LETT, P4171

[4] An Interrupted Fischer Indolization Approach toward Fused Indoline-Containing Natural Products [J].

Boal, Ben W. ;

Schammel, Alex W. ;

Garg, Neil K. .

ORGANIC LETTERS, 2009, 11 (15) :3458-3461

[5] Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines:: Application in the construction of the communesin ring system [J].

Crawley, Seth L. ;

Funk, Raymond L. .

ORGANIC LETTERS, 2006, 8 (18) :3995-3998

[6] A synthetic approach to nomofungin/communesin B [J].

Crawley, SL ;

Funk, RL .

ORGANIC LETTERS, 2003, 5 (18) :3169-3171

[7] Communesins G and H, new alkaloids from the psychrotolerant fungus Penicillium rivulum [J].

Dalsgaard, PW ;

Blunt, JW ;

Munro, MHG ;

Frisvad, JC ;

Christophersen, C .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (02) :258-261

[8] Exploratory studies toward a total synthesis of the marine ascidian metabolite perophoramidine [J].

Evans, Michael A. ;

Sacher, Joshua R. ;

Weinreb, Steven M. .

TETRAHEDRON, 2009, 65 (33) :6712-6719

[9] Indol-2-one intermediates:: Mechanistic evidence and synthetic utility.: Total syntheses of (±)-flustramines A and C [J].

Fuchs, JR ;

Funk, RL .

ORGANIC LETTERS, 2005, 7 (04) :677-680

[10] Total synthesis of (±)-perophoramidine [J].

Fuchs, JR ;

Funk, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5068-5069

← 1 2 3 →