Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue
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.
Winter, Dana K.,Endoma-Arias, Mary Ann,Hudlicky, Tomas,Beutler, John A.,Porco, John A.
p. 7617 - 7626
(2013/09/02)
Synthesis and biological evaluation of ABCD ring fragments of the kibdelones
Arylation goes platinum: The synthesis of the ABCD ring fragments of the kibdelones has been achieved through a novel PtIV-catalyzed arylation of a quinone monoketal followed by photocyclization (see scheme). Biological evaluation in the NCI 60-cell screen revealed that the kibdelone ABCD ring analogues were about 2000 times less active than kibdelones B and C, suggesting that the tetrahydroxanthone structure of the kibdelones is crucial for cytotoxicity. Copyright
Sloman, David L.,Mitasev, Branko,Scully, Stephen S.,Beutler, John A.,Porco Jr., John A.
p. 2511 - 2515
(2011/05/04)
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