Total Synthesis of Dictyodendrins B and E

被引：54

作者：

Liang, Jingjing ^{[1
]}

Hu, Weimin ^{[1
]}

Tao, Pengyu ^{[1
]}

Jia, Yanxing ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 11期

基金：

中国国家自然科学基金;

关键词：

CASCADE REACTIONS; ATOM ECONOMY; TELOMERASE; INDOLES; HETEROANNULATION; INHIBITORS; TARGET; TOOL;

D O I：

10.1021/jo400841d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The concise synthesis of the novel telomerase inhibitors dictyodendrins B and E was completed in only 9 and 11 steps (longest linear sequence). The highly convergent strategy employed a palladium-catalyzed Larock indole synthesis and a palladium-mediated one-pot consecutive Buchwald-Hartwig amination/C H activation reaction as key steps. The present synthesis exhibits respectable levels of atom-, redox-, and step-economy.

引用

页码：5810 / 5815

页数：6

共 34 条

[1] Synthesis of the pyrrolo[2,3-c]carbazole core of the dictyodendrins [J].

Ayats, Carles ;

Soley, Roger ;

Albericio, Fernando ;

Alvarez, Mercedes .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (05) :860-862

[2] N-H carbazole synthesis from 2-chloroanilines via consecutive amination and C-H activation [J].

Bedford, Robin B. ;

Betham, Michael .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9403-9410

[3] Synthesis-driven mapping of the dictyodendrin alkaloids [J].

Buchgraber, Philipp ;

Domostoj, Mathias M. ;

Scheiper, Bodo ;

Wirtz, Conny ;

Mynott, Richard ;

Rust, Joerg ;

Fuerstner, Alois .

TETRAHEDRON, 2009, 65 (33) :6519-6534

[4] Redox Economy in Organic Synthesis [J].

Burns, Noah Z. ;

Baran, Phil S. ;

Hoffmann, Reinhard W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2854-2867

[5] C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products [J].

Chen, David Y. -K. ;

Youn, So Won .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9452-9474

[6] SYNTHESIS OF SUBSTITUTED DIBENZOPHOSPHOLES .2. SYNTHESES OF INTERMEDIATE BIPHENYLS AND QUATERPHENYLS [J].

CORNFORTH, J ;

SIERAKOWSKI, AF ;

WALLACE, TW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (10) :2299-2315

[7] Total syntheses of the telomerase inhibitors dictyodendrin B, C, and E [J].

Fuerstner, Alois ;

Domostoj, Mathias M. ;

Scheiper, Bodo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (24) :8087-8094

[8] Total synthesis of dictyodendrin B [J].

Fürstner, A ;

Domostoj, MM ;

Scheiper, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11620-11621

[9] Aiming for the Ideal Synthesis [J].

Gaich, Tanja ;

Baran, Phil S. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14) :4657-4673

[10] Synthesis of 1,6-dihydropyrrolo[2,3-g]indazoles using Larock indole annulation [J].

Gavara, Laurent ;

Anizon, Fabrice ;

Moreau, Pascale .

TETRAHEDRON, 2011, 67 (38) :7330-7335

← 1 2 3 4 →