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

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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