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Synlett 1995; 1995(1): 49-50
DOI: 10.1055/s-1995-4874
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Synthesis of 4-Hydroxy-3-Substituted Indoles and Indolequinones via an 3-Acetyloxy-4-oxo-4,5,6,7-tetrahydroindole Intermediate

Eric D. Edstrom*
  • *Department of Chemistry and Biochemistry, Utah State University Logan, Utah 84322-0300, USA
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Publication History

Publication Date:
31 December 2000 (online)

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The synthesis of 3-benzyloxycarbonyl-4-hydroxyindole (6) and indolequinones 7a,b from a common-3-acetyloxy-4-oxo-4,5,6,7-tetrahydroindole intermediate 3 is described. A one-step conversion of 3 into 3-trifluoromethanesulfonyloxytetrahydroindole 4 is highlighted and provides a versatile intermediate which undergoes mild palladium-catalyzed carbonylations. Successive oxidations provided the indolequinones 7a,b.

3-Acetyloxy-4-oxo-tetrahydroindole - 4-Hydroxyindole - Indolequinones - Carbonylation

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