Palladium-mediated C-N, C-C, and C-O functionalization of azolopyrimidines: a new total synthesis of variolin B

被引：16

作者：

Baeza, Alejandro ^{[1
]}

Mendiola, Javier ^{[2
]}

Burgos, Carolina ^{[1
]}

Alvarez-Builla, Julio ^{[1
]}

Vaquero, Juan J. ^{[1
]}

机构：

[1] Univ Alcala, Dept Quim Organ, Madrid 28871, Spain

[2] Ctr Invest Lilly, Madrid 28108, Spain

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 25期

关键词：

variolin B; total synthesis; palladium-mediated C-N; C-C and C-O; pyrido[3 ',2 ': 4,5]pyrrolo[1,2-c]pyrimidine; N-tosylmethyl dichloro-formimide;

D O I：

10.1016/j.tetlet.2008.04.063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new total synthesis of the alkaloid variolin B is achieved by a selective and sequential palladium-mediated functionalization of a trihalo-substituted pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine. This intermediate is obtained by a new heterocyclization reaction between an appropriate bromomethyl azaindole and N-tosylmethyl dichloroformimide. The methodology may be effective for the synthesis of some analogs by substitution on the relatively unexplored C4 and C9 positions of the alkaloid. (C) 2008 Elsevier Ltd. All rights reserved.

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页码：4073 / 4077

页数：5

相关论文

共 30 条

[1] Total syntheses of variolin B and deoxyvariolin B [J].

Ahaidar, A ;

Fernández, D ;

Danelón, G ;

Cuevas, C ;

Manzanares, I ;

Albericio, F ;

Joule, JA ;

Alvarez, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :10020-10029

[2] Synthesis of variolin B [J].

Ahaidar, A ;

Fernández, D ;

Pérez, O ;

Danelón, G ;

Cuevas, C ;

Manzanares, I ;

Albericio, F ;

Joule, JA ;

Alvarez, M .

TETRAHEDRON LETTERS, 2003, 44 (33) :6191-6194

[3] Synthesis of deoxyvariolin B [J].

Alvarez, M ;

Fernández, D ;

Joule, JA .

TETRAHEDRON LETTERS, 2001, 42 (02) :315-317

[4]

ALVAREZ M, 2002, Patent No. 02012240

[5] The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].

Anderson, Kevin W. ;

Ikawa, Takashi ;

Tundel, Rachel E. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695

[6] Concise total syntheses of variolin B and deoxyvariolin B [J].

Anderson, RJ ;

Hill, JB ;

Morris, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6204-6212

[7] Total synthesis of variolin B [J].

Anderson, RJ ;

Morris, JC .

TETRAHEDRON LETTERS, 2001, 42 (49) :8697-8699

[8] Studies toward the total synthesis of the variolins: rapid entry to the core structure [J].

Anderson, RJ ;

Morris, JC .

TETRAHEDRON LETTERS, 2001, 42 (02) :311-313

[9] Selective palladium-catalyzed amination of the heterocyclic core of variolins [J].

Baeza, Alejandro ;

Burgos, Carolina ;

Alvarez-Builla, Julio ;

Vaquero, Juan J. .

TETRAHEDRON LETTERS, 2007, 48 (14) :2597-2601

[10] HALOGENATION OF PYRIDINIUM-N-(2'-PYRIDYL)AMINIDE - AN EASY SYNTHESIS OF HALO-2-AMINOPYRIDINES [J].

BURGOS, C ;

DELGADO, F ;

GARCIANAVIO, JL ;

IZQUIERDO, ML ;

ALVAREZBUILLA, J .

TETRAHEDRON, 1995, 51 (31) :8649-8654