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Synthesis 1999; 1999(1): 80-84
DOI: 10.1055/s-1999-3670
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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
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Publication Date:
31 December 1999 (online)

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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

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