Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue

  • J Org Chem. 2013 Aug 2;78(15):7617-26. doi: 10.1021/jo401169z.
Dana K Winter  1 ,  Mary Ann Endoma-Arias ,  Tomas Hudlicky ,  John A Beutler ,  John A Porco Jr
Affiliations
  • 1. Department of Chemistry, Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
PMID: 23834060 DOI: 10.1021/jo401169z
Abstract

The total synthesis of kibdelone A has been accomplished via In(III)-catalyzed arylation of a heterocyclic quinone monoketal and iodine-mediated oxidative photochemical electrocyclization for construction of the ABCD ring moiety. Enzymatic dihydroxylation of methyl 2-halobenzoate substrates was employed for synthesis of activated 2-halo-cyclohexene F-ring fragments. A one pot oxa-Michael/Friedel-Crafts process allowed access to the first simplified DEF ring analogues of the kibdelones.

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