Download PDF
Synthesis 2000; 2000(5): 677-680
DOI: 10.1055/s-2000-6398
paper
© 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 Echinotinctone, A Fungal Fluorone Pigment

Matthias Rüth* , Wolfgang Steglich *
  • *Institut für Organische Chemie der Universität, Butenandtstr. 5-13, 81377 München, Germany; Fax + 49(89)21 80 77 56; E-mail: wos@cup.uni-muenchen.de
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Echinotinctone (3) is formed by acid-catalyzed condensation of 1,2,4-trihydroxytoluene (1) with orcylaldehyde (2), a reaction mimicking the probable biosynthesis. A more efficient stepwise synthesis proceeds via the benzophenone intermediate 11, which can be converted to 2,6-dihydroxy-1,8-dimethyl-3H-xanthen-3-one (3) by LiAlH4 reduction and subsequent acid-catalyzed ring closure.

natural products - basidiomycetes - quinone methides - xanthenes - fluorones - phenols - cyclizations - benzylations

      >