Access to a Welwitindolinone Core Using Sequential Cycloadditions

被引：93

作者：

Trost, Barry M. ^{[1
]}

McDougall, Patrick J. ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 16期

关键词：

METHYLWELWITINDOLINONE-C ISOTHIOCYANATE; MULTIPLE-DRUG RESISTANCE; DIELS-ALDER REACTION; TRIMETHYLENEMETHANE; WELWISTATIN; ALKALOIDS; FURANS; BOND;

D O I：

10.1021/ol901499b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise approach to the core skeleton of the welwitindolinone alkaloids was developed on the basis of sequential cycloaddition reactions. First, a palladium catalyzed enantioselective [6 + 3] trimethylenemethane cycloaddition onto a tropone nucleus was used to generate the requisite bicyclo[4.3.1]decadiene. Subsequent modifications to the cycloadduct allowed for an intramolecular [4 + 2] cycloaddition to generate the oxindole and complete the core of the natural product family.

引用

收藏

页码：3782 / 3785

页数：4

相关论文

共 25 条

[1] TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .2. ADDITION TO AROMATIC-MOLECULES - CATALYSIS OF BUCHNER SYNTHESIS OF CYCLOHEPTATRIENES [J].

ANCIAUX, AJ ;

DEMONCEAU, A ;

NOELS, AF ;

HUBERT, AJ ;

WARIN, R ;

TEYSSIE, P .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (05) :873-876

[2] Synthetic studies on N-methylwelwitindolinone C isothiocyanate (welwistatin) and related substructures [J].

Avendaño, C ;

Menéndez, JC .

CURRENT ORGANIC SYNTHESIS, 2004, 1 (01) :65-82

[3] Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G [J].

Baran, PS ;

Richter, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15394-15396

[4] SYNTHETIC EXPERIMENTS IN THE CYCLOHEPTATRIENONE SERIES .2. 4-KETOCYCLOHEPTATRIENECARBOXYLIC ACID [J].

BARTELSKEITH, JR ;

JOHNSON, AW ;

LANGEMANN, A .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (NOV) :4461-4466

[5] Singlet oxygen conversion of indoles into α,β-unsaturated oxindoles in model compounds related to the welwitindolinone alkaloids [J].

Boissel, Valerie ;

Simpkins, Nigel S. ;

Bhalay, Gurdip .

TETRAHEDRON LETTERS, 2009, 50 (26) :3283-3286

[6] TURNING THE CORNER: RECENT ADVANCES IN THE SYNTHESIS OF THE WELWITINDOLINONES [J].

Brown, Lauren E. ;

Konopelski, Joseph P. .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2008, 40 (05) :411-+

[7]

BURGESS EM, 1988, ORG SYNTH, V6, P789

[8] Synthesis of 1,3-difunctionalized amine derivatives through selective C-H bond oxidation [J].

Espino, CG ;

Wehn, PM ;

Chow, J ;

Du Bois, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6935-6936

[9] Oxidized welwitindolinones from terrestrial Fischerella spp. [J].

Jimenez, JI ;

Huber, U ;

Moore, RE ;

Patterson, GML .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (04) :569-572

[10] Intramolecular amidofuran cycloadditions across an indole π-bond:: An efficient approach to the Aspidosperma and Strychnos ABCE core [J].

Lynch, SM ;

Bur, SK ;

Padwa, A .

ORGANIC LETTERS, 2002, 4 (26) :4643-4645