Download PDF
Synlett 2001; 2001(9): 1428-1430
DOI: 10.1055/s-2001-16782
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.

Novel Use of a Selenoalkyne Within Untraditionally Mild Dötz Benzannulation Processes; Total Synthesis of a Calceolaria andina L. Natural Hydroxylated Naphthoquinone

John J. Caldwell* , Robert Colman, William J. Kerr, Euan J. Magennis
  • *Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, Scotland, U.K.; Fax + 44 141 548 4246; E-mail: w.kerr@strath.ac.uk
Further Information

Publication History

Publication Date:
28 August 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

A total synthesis of the Calceolaria andina L. extract 2-(1,1-dimethyl-2-propenyl)-3-hydroxy-1,4-naphthalenedione is described incorporating the first reported Dötz benzannulation of a selenoalkyne. Importantly, it has been shown that it is possible to effect this annulation at ambient temperature under dry state conditions with a significant improvement in cyclisation yield.

carbene complexes - chromium - Dötz benzannulation - dry state techniques - selenium