Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy

被引：198

作者：

Beck, Elizabeth M. ^{[1
]}

Hatley, Richard ^{[2
]}

Gaunt, Matthew J. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 16期

基金：

英国工程与自然科学研究理事会;

关键词：

C-H activation; natural products; palladium;

D O I：

10.1002/anie.200705005

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Iterative and regioselective metal-catalyzed C-H bondfunctionalization has been utilizedto develop a strategy for the first total synthesis of the pyrrole alkaloid rhazinicine (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3004 / 3007

页数：4

共 42 条

[1]

Banwell MG, 2006, ARKIVOC, P163

[2] Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi [J].

Banwell, MG ;

Edwards, AJ ;

Jolliffe, KA ;

Smith, JA ;

Hamel, E ;

Verdier-Pinard, P .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) :296-305

[3] A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization [J].

Baran, PS ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7904-7905

[4] The chemistry and biology of rhazinilam and analogues [J].

Baudoin, O ;

Guénard, D ;

Guéritte, F .

MINI-REVIEWS IN ORGANIC CHEMISTRY, 2004, 1 (03) :333-341

[5] Synthesis and biological evaluation of A-ring biaryl-carbamate analogues of rhazinilam [J].

Baudoin, O ;

Claveau, F ;

Thoret, S ;

Herrbach, A ;

Guénard, D ;

Guéritte, F .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) :3395-3400

[6] Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].

Beck, EM ;

Grimster, NP ;

Hatley, R ;

Gaunt, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529

[7] Concise synthesis of (±)-rhazinilam through direct coupling [J].

Bowie, AL ;

Hughes, CC ;

Trauner, D .

ORGANIC LETTERS, 2005, 7 (23) :5207-5209

[8] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[9] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

[10]

Covell D. J., 2006, ANGEW CHEM, V118, P8397

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