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Synthesis 2007(19): 3044-3050  
DOI: 10.1055/s-2007-983893
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Substituted Pyranoquinolinones from 2,4-Dihydroxy­quinoline: Total Synthesis of Zanthosimuline, cis-3′,4′-Dihydroxy-3′,4′-di­hydroflindersine, and Orixalone D

Xue Wang, Yong Rok Lee*
School of Chemical Engineering and Technology, Yeungnam University, Gyeongsan 712-749, South Korea
Fax: +82(53)8104631; e-Mail: yrlee@ynu.ac.kr;
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Publication History

Received 31 May 2007
Publication Date:
11 September 2007 (online)

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Abstract

A convenient and efficient synthesis of pyranoquinoli­nones was achieved using the ethylenediamine diacetate catalyzed reactions of 2,4-dihydroxyquinoline and a variety of α,β-unsaturated aldehydes in good yield. The key feature of these reactions is the formal [3+3] cycloaddition. This new methodology was applied successfully to the total synthesis of naturally occurring pyranoquinolinone alkaloids, zanthosimuline, cis-3′,4′-dihydroxy-3′,4′-dihydroflindersine, and orixalone D.

Key words

pyranoquinolinones - formal [3+3] cycloaddition - zanthosimuline - cis-3′,4′-dihydroxy-3′4′-dihydroflindersine - orixalone D