Total synthesis of 8-deshydroxyajudazol B |
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Authors: | Birkett Stephen Ganame Danny Hawkins Bill C Meiries Sébastien Quach Tim Rizzacasa Mark A |
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Institution: | School of Chemistry, The Bio21 Institute, The University of Melbourne, Victoria 3010, Australia. |
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Abstract: | The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels-Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira coupling to form the C18-C19 bond. Partial alkyne reduction then afforded the target 4. |
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