PDF herunterladen
Synthesis 1999; 1999(1): 80-84
DOI: 10.1055/s-1999-3670
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.

Synthetic Studies Towards the Total Synthesis of Olivin Using Fischer Carbene Complexes: Synthesis of the 1,6,8-Trioxygenated Tricyclic Core via the Benzannulation Reaction

Ross A. Miller* , Adam M. Gilbert, Song Xue, William D. Wulff
  • *Department of Chemistry, Searle Chemistry Laboratory, The University of Chicago, Chicago, Illinois 60637, USA; Fax +1(7 73)7 02-08 05; E-mail: wulff@rainbow.uchicago.edu
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 1999 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

A synthesis of a model for the tricyclic core of olivin is developed which begins with the benzannulation of a 2,4-dioxygenated aryl Fischer carbene complex. Completion of the synthesis of the model system involves an intramolecular Friedel-Crafts cyclization and a triflate reduction of the oxygen substituent at the C-10 position. The proper choice of oxygen substituents on the carbene complex will permit this strategy to be utilized in the synthesis of olivomycin A where the oxygens in the C-2 and C-6 positions will need to be differentiated.

benzannulation - Fischer carbene complexes - olivin - Friedel-Crafts cyclization