First Total Synthesis of the Bioactive Anthraquinone Kwanzoquinone C and Related Natural Products by a Diels–Alder Approach

LF Tietze, KM Gericke, C Güntner

Index: Tietze, Lutz F.; Gericke, Kersten M.; Guentner, Carlos European Journal of Organic Chemistry, 2006 , # 21 p. 4910 - 4915

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Citation Number: 8

Abstract

Abstract The first total synthesis of the novel anticancer agent kwanzoquinone C (1), an anthraquinone glycoside which has been isolated from extracts of the roots of orange daylilies (Kaempfer)(Hemerocallisfulva) is reported. The strategy involves the preparation of the tetrasubstituted 1, 3-butadiene 6 by an electrocyclic conrotatory ring opening of the cyclobutanone rac-11, which is obtained by a [2+ 2] cycloaddition. Diels–Alder reaction of ...