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  • Title: Total synthesis of 8-deshydroxyajudazol B.
    Author: Birkett S, Ganame D, Hawkins BC, Meiries S, Quach T, Rizzacasa MA.
    Journal: Org Lett; 2011 Apr 15; 13(8):1964-7. PubMed ID: 21410165.
    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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