Oxidative Coupling as a Biomimetic Approach to the Synthesis of Scytonemin

被引：37

作者：

Ekebergh, Andreas ^{[1
]}

Karlsson, Isabella ^{[2
]}

Mete, Rudi ^{[2
]}

Pan, Ye ^{[1
]}

Borje, Anna ^{[2
]}

Martensson, Jerker ^{[1
]}

机构：

[1] Chalmers, Dept Chem & Biol Engn Organ Chem, SE-41296 Gothenburg, Sweden

[2] Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 16期

基金：

瑞典研究理事会;

关键词：

SUNSCREEN SCYTONEMIN; PIGMENT; CYANOBACTERIA; BIOSYNTHESIS; DERIVATIVES; SCOPE; ARYL;

D O I：

10.1021/ol201812n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the dimeric alkaloid pigment scytonemin is described. The key transformations In Its synthesis from 3-indole acetic acid are a Heck carbocyclization and a Suzuki-Miyaura cross-coupling, orchestrated In a stereospecific tandem fashion, followed by a biosynthetically inspired oxidative dimerization. The tandem sequence generates a tetracyclic (E)-3-(arylidene)-3,4-dihydrocyclopenta[b]indol-2(1H)-one that is subsequently dimerized into the unique homodimeric core structure of scytonemin.

引用

页码：4458 / 4461

页数：4

共 20 条

[1] Tandem Heck-Suzuki-Miyaura reaction: Application to the synthesis of constrained analogues of combretastatin A-4 [J].

Arthuis, Martin ;

Pontikis, Renee ;

Florent, Jean-Claude .

TETRAHEDRON LETTERS, 2007, 48 (36) :6397-6400

[2] An Enzymatic Cyclopentyl[b]indole Formation Involved in Scytonemin Biosynthesis [J].

Balskus, Emily P. ;

Walsh, Christopher T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) :14648-+

[3] Investigating the Initial Steps in the Biosynthesis of Cyanobacterial Sunscreen Scytonemin [J].

Balskus, Emily P. ;

Walsh, Christopher T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (46) :15260-+

[4] Total synthesis of (±)-chartelline C [J].

Baran, Phil S. ;

Shenvi, Ryan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) :14028-14029

[5] A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].

Cheung, WS ;

Patch, RJ ;

Player, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744

[6] Ultraviolet radiation screening compounds [J].

Cockell, CS ;

Knowland, J .

BIOLOGICAL REVIEWS, 1999, 74 (03) :311-345

[7] Intermolecular enolate heterocoupling: Scope, mechanism, and application [J].

DeMartino, Michael P. ;

Chen, Ke ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11546-11560

[8] Synthesis of substituted carbazoles and β-carbolines by cyclization of diketoindole derivatives [J].

Duval, E ;

Cuny, GD .

TETRAHEDRON LETTERS, 2004, 45 (28) :5411-5413

[9] CHARACTERIZATION AND BIOLOGICAL IMPLICATIONS OF SCYTONEMIN, A CYANOBACTERIAL SHEATH PIGMENT [J].

GARCIAPICHEL, F ;

CASTENHOLZ, RW .

JOURNAL OF PHYCOLOGY, 1991, 27 (03) :395-409

[10] Stereoselective homocoupling of enolate anion promoted by hypervalent iodine compound [J].

Kim, JW ;

Lee, JJ ;

Lee, SH ;

Ahn, KH .

SYNTHETIC COMMUNICATIONS, 1998, 28 (07) :1287-1292

← 1 2 →