Total synthesis of cavicularin and riccardin C: Addressing the synthesis of an arene that adopts a boat configuration

被引：64

作者：

Harrowven, DC ^{[1
]}

Woodcock, T

Howes, PD

机构：

[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England

[2] GlaxoSmithKline Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 25期

关键词：

arenes; macrocycles; radical reactions ring; contraction; total synthesis;

D O I：

10.1002/anie.200500466

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A transannular ring contraction induced by the addition of an aryl radical intermediate to a proximal arene facilitated the construction of the highly strained macrocyclic core of cavicularin (1). The precursor, an iodinated derivative of another natural product, riccardin C, was prepared from four commercially available arenes in a highly convergent sequence. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3899 / 3901

页数：3

共 24 条

[1] PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION [J].

AMES, DE ;

OPALKO, A .

TETRAHEDRON, 1984, 40 (10) :1919-1925

[2]

ASAKAWA Y, 1983, J ORG CHEM, V48, P2164, DOI 10.1021/jo00161a009

[3] RICCARDIN-C, A NOVEL CYCLIC BIBENZYL DERIVATIVE FROM REBOULIA-HEMISPHAERICA [J].

ASAKAWA, Y ;

MATSUDA, R .

PHYTOCHEMISTRY, 1982, 21 (08) :2143-2144

[4]

Beckwith A. L. J., 2004, ANGEW CHEM, V116, P97

[5] The mechanism of Bu3SnH-mediated homolytic aromatic substitution [J].

Beckwith, ALJ ;

Bowry, VW ;

Bowman, WR ;

Mann, E ;

Parr, J ;

Storey, JMD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :95-98

[6] On the verge of axial chirality: Atroposelective synthesis of the AB-biaryl fragment of vancomycin [J].

Bringmann, G ;

Menche, D ;

Muhlbacher, J ;

Reichert, M ;

Saito, N ;

Pfeiffer, SS ;

Lipshutz, BH .

ORGANIC LETTERS, 2002, 4 (17) :2833-2836

[7]

CHATGILIALOGLU C, 2003, ORGANOSILANES RADICA

[8]

DANN O, 1984, LIEBIGS ANN CHEM, P409, DOI 10.1002/jlac.198419840302

[9] AN EFFICIENT AND SELECTIVE METHOD FOR THE PREPARATION OF IODOPHENOLS [J].

EDGAR, KJ ;

FALLING, SN .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5287-5291

[10]

Eicher T, 1998, EUR J ORG CHEM, V1998, P877

← 1 2 3 →