Catalytic intramolecular crossed aldehyde-ketone benzoin reactions: A novel synthesis of functionalized preanthraquinones

被引：173

作者：

Hachisu, Y

Bode, JW

Suzuki, K

机构：

[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Okayama, Tokyo 1528551, Japan

[2] Japan Sci & Technol Corp, CREST, Meguro Ku, Okayama, Tokyo 1528551, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 28期

关键词：

ANTIBIOTICS;

D O I：

10.1021/ja035308f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereochemically and functionally rich polycyclic compounds are obtained by the first crossed aldehyde-ketone benzoin reaction in excellent yield under mild reaction conditions (5-20 mol % thiazolium salt, 10-70 mol % DBU, tBuOH, 40°C, 30 min). This novel catalytic methodology offers a convenient approach to sophisticated molecular architectures useful for the stereocontrolled construction of polycyclic compounds as well as the fully regiocontrolled synthesis of anthra- and naphthoquinones. Copyright © 2003 American Chemical Society.

引用

页码：8432 / 8433

页数：2

共 27 条

[1] Structural incongruities of coleophomone natural products: insights by total synthesis of a semi-synthetic derivative [J].