Rapid access to the welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones

被引：47

作者：

Baudoux, J ^{[1
]}

Blake, AJ ^{[1
]}

Simpkins, NS ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 19期

关键词：

D O I：

10.1021/ol051239t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very rapid access to cyclohexanone-bridged indole systems was established by an acid-mediated ring closure of appropriately substituted indole aldehydes, which involved an apparent disproportionation of an aldol-like intermediate. One of the bridged indole intermediates was further transformed into an oxindole having the essential skeleton of the Welwitindolinone alkaloids.

引用

页码：4087 / 4089

页数：3

共 17 条

[1] A MILD AND SELECTIVE C-3 REDUCTIVE ALKYLATION OF INDOLES [J].

APPLETON, JE ;

DACK, KN ;

GREEN, AD ;

STEELE, J .

TETRAHEDRON LETTERS, 1993, 34 (09) :1529-1532

[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] The enantioselective generation of bridgehead enolates [J].

Blake, AJ ;

Giblin, GMP ;

Kirk, DT ;

Simpkins, NS ;

Wilson, C .

CHEMICAL COMMUNICATIONS, 2001, (24) :2668-2669

[4] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[5] 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

[6] Highly active and selective catalysts for the formation of α-aryl ketones [J].

Fox, JM ;

Huang, XH ;

Chieffi, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370

[7] Bridgehead enolates: Substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases [J].

Giblin, GMP ;

Kirk, DT ;

Mitchell, L ;

Simpkins, NS .

ORGANIC LETTERS, 2003, 5 (10) :1673-1675

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

Jimenez, JI ;

Huber, U ;

Moore, RE ;

Patterson, GML .

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

[9] Rhodium-catalyzed decomposition of indole-substituted α-diazo-β-keto esters:: three different reactions based on indole oxidation state [J].

Jung, ME ;

Slowinski, F .

TETRAHEDRON LETTERS, 2001, 42 (39) :6835-6838

[10]

López-Alvarado P, 2002, EUR J ORG CHEM, V2002, P1702

← 1 2 →