Progress toward synthesis of diazonamide A. Preparation of a 3-(oxazol-5-yl)-4-trifluoromethyl-sulfonyloxyindole and its use in biaryl coupling reactions.
[formula: see text] The synthesis of a 3-oxazol-5-yl-indole-4-triflate is described, featuring a Schölkopf reaction to prepare the oxazole. In addition, the participation of this intermediate in biaryl coupling reactions toward the total synthesis of the natural product diazonamide A is presented.
Vedejs
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Department of Chemistry, University of Wisconsin-Madison 53706, USA. edved@umich.edu
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D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008698:Mesylates / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D013816:Thermodynamics
C408863:1-(tert-butoxycarbonyl)-4-trifluoromethylsulfonyloxy-3-(oxazol-5-yl)indole; D006576:Heterocyclic Compounds, 4 or More Rings; D008698:Mesylates; D010080:Oxazoles; C408862:diazonamide A