Dearomatizing cyclization of arylsulfonylalkoxymethyl lithiums: A route to the podophyllotoxin skeleton

被引：38

作者：

Clayden, J ^{[1
]}

Kenworthy, MN ^{[1
]}

Helliwell, M ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/ol0340585

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Graphics The phenylsulfonyl group promotes the dearomatizing cyclization of tethered organolithiums onto aromatic rings. With an ether tether, the cyclizations create a new tetrahydrofuran ring, and both cyclization and subsequent electrophilic quenches proceed with high levels of diastereoselectivity. The sulfonyl group can be removed from the cyclized products oxidatively or reductively. The dearomatizing cyclization of a naphthyl sulfone was used in the synthesis of a close structural analogue of podophyllotoxin.

引用

页码：831 / 834

页数：4

共 59 条

[1] Highly diastereoselective aziridination of imines with trimethylsilyldiazomethane.: Subsequent silyl substitution with electrophiles, ring opening, and metalation of C-silylaziridines -: A cornucopia of highly selective transformations [J].

Aggarwal, VK ;

Alonso, E ;

Ferrara, M ;

Spey, SE .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (07) :2335-2344

[2] Highly selective aziridination of imines using trimethylsilyldiazomethane and applications of C-silylaziridines in synthesis [J].

Aggarwal, VK ;

Ferrara, M .

ORGANIC LETTERS, 2000, 2 (25) :4107-4110

[3] Synthesis of a potent (±)-4-(2-hydroxyphenyl) analogue of the acromelic acids by dearomatising cyclisation of a lithiated N-p-methoxybenzyl-4-methoxy-l-naphthamide [J].

Ahmed, A ;

Bragg, RA ;

Clayden, J ;

Tchabanenko, K .

TETRAHEDRON LETTERS, 2001, 42 (20) :3407-3410

[4] Dearomatising cyclisations of lithiated N-benzylbenzamides [J].

Ahmed, A ;

Clayden, J ;

Yasin, SA .

CHEMICAL COMMUNICATIONS, 1999, (03) :231-232

[5] Anionic cyclisations of an N-benzyl naphthamide:: a route to benzo[e]isoindolones [J].

Ahmed, A ;

Clayden, J ;

Rowley, M .

CHEMICAL COMMUNICATIONS, 1998, (03) :297-298

[6]

ANDERSON JC, 1990, SYNLETT, P107

[7] ASYMMETRIC TOTAL SYNTHESIS OF (-)-PODOPHYLLOTOXIN [J].

ANDREWS, RC ;

TEAGUE, SJ ;

MEYERS, AI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7854-7858

[8]

Ayres D.C., 1990, CHEM BIOL CLIN PROPE

[9] Additions to functionalized arenes with concurrent dearomatization [J].

Bach, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (07) :729-730

[10] Facile allylative dearomatization catalyzed by palladium [J].

Bao, M ;

Nakamura, H ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :759-760

← 1 2 3 4 5 6 →