Approaches to N-Methylwelwitindolinone C Isothiocyanate: Facile Synthesis of the Tetracyclic Core

被引：36

作者：

Heidebrecht, Richard W., Jr. ^{[1
]}

Gulledge, Brian ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 11期

基金：

美国国家卫生研究院;

关键词：

(+/-)-WELWITINDOLINONE-A ISONITRILE; WELWITINDOLINONE; INDOLES; HAPALINDOLES; WELWISTATIN; SKELETON; FISCHERINDOLES; CYCLIZATION; ALKALOIDS; ACYLATION;

D O I：

10.1021/ol1006373

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a functionalized, tetracyclic core of N-methylwelwitindolinone C isothiocyanate is reported. The approach features a convergent coupling between an indole iminium ion and a highly functionalized vinylogous silyl ketene acetal followed by an intramolecular palladium-catalyzed cyclization that proceeds via an enolate arylation.

引用

页码：2492 / 2495

页数：4

共 37 条

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

Avendaño, C ;

Menéndez, JC .

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

[2] 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

[3] Rapid access to the welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones [J].

Baudoux, J ;

Blake, AJ ;

Simpkins, NS .

ORGANIC LETTERS, 2005, 7 (19) :4087-4089

[4] Bridgehead enolates and bridgehead alkenes in a welwistatin model series [J].

Boissel, Valerie ;

Simpkins, Nigel S. ;

Bhalay, Gurdip ;

Blake, Alexander J. ;

Lewis, William .

CHEMICAL COMMUNICATIONS, 2009, (11) :1398-1400

[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] HETEROCYCLIC AROMATIC ANIONS WITH 4N+2-PI-ELECTRONS [J].

BORDWELL, FG ;

FRIED, HE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4218-4223

[7] Synthesis of the Bicyclic Welwitindolinone Core via an Alkylation/Cyclization Cascade Reaction [J].

Brailsford, John A. ;

Lauchli, Ryan ;

Shea, Kenneth J. .

ORGANIC LETTERS, 2009, 11 (22) :5330-5333

[8] 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-+

[9]

COMINS DL, 1986, TETRAHEDRON LETT, V27, P1869, DOI 10.1016/S0040-4039(00)84397-X

[10] Aryllead(IV) reagents in synthesis:: Formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate [J].

Deng, HB ;

Konopelski, JP .

ORGANIC LETTERS, 2001, 3 (19) :3001-3004

← 1 2 3 4 →