Asymmetric Total Synthesis of (+)-Merobatzelladine B

被引：44

作者：

Babij, Nicholas R. ^{[1
]}

Wolfe, John P. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 17期

关键词：

alkaloids; asymmetric synthesis; natural products; palladium; total synthesis; PD-CATALYZED CARBOAMINATION; ENANTIOSELECTIVE TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; GUANIDINE DERIVATIVES; IMIDAZOLIDIN-2-ONES; (-)-BATZELLADINE-D; LIMITATIONS; REVISION; IMINES; SCOPE;

D O I：

10.1002/anie.201201001

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Putting the syn in synthesis: The first total synthesis of (+)-merobatzelladineB was accomplished using an iterative sequence of stereoselective palladium-catalyzed alkene carboamination reactions for formation of two of the three rings. This represents a new strategy for the generation of polycyclic guanidine natural products, and provides access to compounds with a synrelationship between the C6 hydrogen atom and the C8 alkyl group. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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页码：4128 / 4130

页数：3

相关论文

共 32 条

[1] Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4+2]-annulation of vinyl carbodiimides with N-alkyl imines [J].

Arnold, Michael A. ;

Day, Kenneth A. ;

Duron, Sergio G. ;

Gin, David Y. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13255-13260

[2] The tethered Biginelli condensation in natural product synthesis [J].

Aron, ZD ;

Overman, LE .

CHEMICAL COMMUNICATIONS, 2004, (03) :253-265

[3] Natural guanidine derivatives [J].

Berlinck, RGS ;

Kossuga, MH .

NATURAL PRODUCT REPORTS, 2005, 22 (04) :516-550

[4] The chemistry and biology of organic guanidine derivatives [J].

Berlinck, Roberto G. S. ;

Burtoloso, Antonio Carlos B. ;

Kossuga, Miriam H. .

NATURAL PRODUCT REPORTS, 2008, 25 (05) :919-954

[5] The chemistry and biology of organic guanidine derivatives [J].

Berlinck, Roberto G. S. ;

Burtoloso, Antonio Carlos B. ;

Trindade-Silva, Amaro E. ;

Romminger, Stelamar ;

Morais, Raquel P. ;

Bandeira, Karin ;

Mizuno, Carolina M. .

NATURAL PRODUCT REPORTS, 2010, 27 (12) :1871-1907

[6] Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides [J].

Bertrand, MB ;

Wolfe, JP .

TETRAHEDRON, 2005, 61 (26) :6447-6459

[7] Mild Conditions for Pd-Catalyzed Carboamination of N-Protected Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines. Scope, Limitations, and Mechanism of Pyrrolidine Formation [J].

Bertrand, Myra Beaudoin ;

Neukom, Joshua D. ;

Wolfe, John P. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8851-8860

[8] Inhibition of HIV-1 envelope-mediated fusion by synthetic batzelladine analogues [J].

Bewley, CA ;

Ray, S ;

Cohen, F ;

Collins, SK ;

Overman, LE .

JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08) :1319-1324

[9] Synthesis and stereochemical determination of batzelladine C methyl ester [J].

Butters, Michael ;

Davies, Christopher D. ;

Elliott, Mark C. ;

Hill-Cousins, Joseph ;

Kariuki, Benson M. ;

Ooi, Li-ling ;

Wood, John L. ;

Wordingham, Stuart V. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (23) :5001-5009

[10] Enantioselective total synthesis of batzelladine F: Structural revision and stereochemical definition [J].

Cohen, F ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10782-10783

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