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Synthesis 2009(21): 3642-3648  
DOI: 10.1055/s-0029-1217004
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Approach to Methoxyisatins Leading to the Total Synthesis of Ophiuroidine and Other Hydroxytryptanthrins

Jeffrey J. Mason, Tomasz Janosik, Jan Bergman*
Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, 141 57 Huddinge, Sweden
Fax: +46(8)6081501; e-Mail: Jan.Bergman@ki.se;
Further Information

Publication History

Received 9 June 2009
Publication Date:
08 September 2009 (online)

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Abstract

A new method for the preparation of methoxyisatins from the corresponding methoxyanilines is described. The resulting methoxyisatins were used in the syntheses of several methoxytryptanthrin compounds. The natural product ophiuroidine (4,8,9-trihydroxytryptanthrin) was obtained from the appropriate trimethoxy precursor using a microwave-mediated Prey demethylation.

Key words

isatin - tryptanthrin - ophiuroidine - Prey demethylation - microwave irradiation

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