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  • Title: Convergent synthesis and discovery of a natural product-inspired paralog-selective Hsp90 inhibitor.
    Author: Jeso V, Cherry L, Macklin TK, Pan SC, LoGrasso PV, Micalizio GC.
    Journal: Org Lett; 2011 Oct 07; 13(19):5108-11. PubMed ID: 21866939.
    Abstract:
    A convergent synthesis of benzoquinone ansamycin analogs is described that proceeds by a sequence of metallacycle-mediated alkyne-alkyne coupling, followed by site- and stereoselective dihydroxylation and global carbamate formation. These studies have led to (1) validation of alkyne-alkyne coupling to produce geldanamycin analogs that lack the problematic quinone, (2) the discovery that C6-C7 bis-carbamate functionality is compatible with Hsp90 inhibition, and (3) the identification of 1 as a nonquinone geldanamycin-inspired paralog-selective Hsp90 inhibitor.
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