An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10 Catalysis

Jian-Ming Lee; Tsui-Hwa Tseng; Yean-Jang Lee

doi:10.1055/s-2001-18436

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Synthesis 2001(15): 2247-2254
DOI: 10.1055/s-2001-18436

PAPER

An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10 Catalysis

Jian-Ming Lee^a, Tsui-Hwa Tseng^b, Yean-Jang Lee*^a
^a Department of Chemistry, National Changhua University of Education, Changhua, Taiwan, Republic of China
Fax: +886(4)7211190; e-Mail: leeyj@cc.ncue.edu.tw;
^b Institute of Biochemistry, Chung Shan Medical and Dental College, Taiwan, Republic of China

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Publication History

Received 5 July 2001
Publication Date:
05 August 2004 (online)

Abstract
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Abstract

A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.

Key words

montmorillonite K-10 - 4-phenylneoflavonoids - Fries rearrangement

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The X-ray data for 8, 9, 13 are deposited at CCDC as numbers 170003, 170002 and 170001, respectively.