Concise total synthesis of phidianidine A and B |
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| Authors: | Jacob C Buchanan Brandon P Petersen Stephen Chamberland |
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| Institution: | Department of Chemistry, Central Washington University, 400 East University Way, Ellensburg, WA 98926-7539, USA |
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| Abstract: | The shortest total synthesis of cytotoxic indole alkaloids phidianidine A and B is described. Rapid assembly of the 1,2,4-oxadiazole core from a novel N-hydroxyguanidine and the corresponding indole-3-acetic acid chloride led to formal syntheses of phidianidine A and B in only three steps from known compounds. Deprotection under standard conditions provided the trifluoroacetate salts of phidianidine A and B in quantitative yield. |
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| Keywords: | Total synthesis Marine natural product 1 2 4-Oxadiazole Heterocycles Guanidinylation |
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