Total Synthesis of Calothrixins A and B by Palladium-Catalyzed Tandem Cyclization/Cross-Coupling Reaction of Indolylborate

被引：47

作者：

Abe, Takumi ^{[1
]}

Ikeda, Toshiaki ^{[1
]}

Choshi, Tominari ^{[2
]}

Hibino, Satoshi ^{[2
]}

Hatae, Noriyuki ^{[1
]}

Toyata, Eiko ^{[1
]}

Yanada, Reiko ^{[3
]}

Ishikura, Minoru ^{[1
]}

机构：

[1] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

[2] Fukuyama Univ, Fac Pharm & Pharmaceut Sci, Fukuyama, Hiroshima 7290292, Japan

[3] Hiroshima Int Univ, Fac Pharmaceut Sci, Kure, Hiroshima 7370112, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 26期

关键词：

Cross-coupling; Total synthesis; Palladium; Copper; Electrocyclic reactions; BIOMIMETIC SYNTHESIS; PYRIDINIUM CHLOROCHROMATE; CONVENIENT METHOD; OXIDATION; ROUTE; HALIDES; SCOPE;

D O I：

10.1002/ejoc.201200657

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate with vinyl bromide was successfully used in the concise total synthesis of the indolophenanthridine alkaloids, calothrixins A and B.

引用

页码：5018 / 5027

页数：10

共 49 条

[1] Concise Total Synthesis of Calothrixins A and B [J].

Abe, Takumi ;

Ikeda, Toshiaki ;

Yanada, Reiko ;

Ishikura, Minoru .

ORGANIC LETTERS, 2011, 13 (13) :3356-3359

[2] Mechanistic and kinetic studies of palladium catalytic systems [J].

Amatore, C ;

Jutand, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :254-278

[3] A new radical-based route to calothrixin B [J].

Bennasar, ML ;

Roca, T ;

Ferrando, F .

ORGANIC LETTERS, 2006, 8 (04) :561-564

[4] Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones [J].

Bernardo, PH ;

Chai, CLL ;

Heath, GA ;

Mahon, PJ ;

Smith, GD ;

Waring, P ;

Wilkes, BA .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (20) :4958-4963

[5] Friedel-Crafts acylation and metalation strategies in the synthesis of calothrixins A and B [J].

Bernardo, PH ;

Chai, CLL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :8906-8909

[6] A simple and concise route to calothrixin B [J].

Bernardo, PH ;

Chai, CLL ;

Elix, JA .

TETRAHEDRON LETTERS, 2002, 43 (16) :2939-2940

[7] Catalysis of 6π Electrocyclizations [J].

Bishop, Lee M. ;

Barbarow, Jennifer E. ;

Bergman, Robert G. ;

Trauner, Dirk .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) :8100-8103

[8] PROGRESS TOWARDS THE TOTAL SYNTHESIS OF THE BIOACTIVE CALOTHRIXINS A AND B [J].

Choshi, Tominari ;

Hibino, Satoshi .

HETEROCYCLES, 2009, 77 (01) :85-97

[9]

Desimoni G, 1983, NATURAL PRODUCTS SYN

[10] THE OXIDATION OF 2-CYCLOHEXEN-1-ONES TO 2-CYCLOHEXENE-1,4-DIONES [J].

FREER, VJ ;

YATES, P .

CHEMISTRY LETTERS, 1984, (12) :2031-2032

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