Download PDF
Synlett 1995; 1995(1): 49-50
DOI: 10.1055/s-1995-4874
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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