Enantioselective Total Synthesis and Biological Evaluation of (+)-Kibdelone A and a Tetrahydroxanthone Analogue
2013
Winter, Dana K. | Endoma-Arias, Mary Ann | Hudlicky, Tomas | Beutler, John A. | Porco, John A.
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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