A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones

被引：99

作者：

Gerard, B

Jones, G

Porco, JA ^{[1
]}

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

[2] Boston Univ, Ctr Chem Methodol, Boston, MA 02215 USA

[3] Boston Univ, Lib Dev, Boston, MA 02215 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 42期

关键词：

D O I：

10.1021/ja044798o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unified biomimetic approach to the aglain-forbaglin-rocaglamide classes of natural products is reported. The approach involves photogeneration of oxidopyryliums via excited-state intramolecular proton transfer (ESIPT) of 3-hydroxyflavones followed by [3+2] dipolar cycloaddition to the aglain core. An α-ketol (acyloin) rearrangement was employed to transform the aglain core to the rocaglamide framework. This approach was successfully used for the synthesis of the natural product (±)-methyl rocaglate. Copyright © 2004 American Chemical Society.

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页码：13620 / 13621

页数：2

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