1380226-12-9Relevant articles and documents
Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue
Winter, Dana K.,Endoma-Arias, Mary Ann,Hudlicky, Tomas,Beutler, John A.,Porco, John A.
, p. 7617 - 7626 (2013)
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.
Toluene dioxygenase mediated oxidation of halogen-substituted benzoate esters
Semak, Vladislav,Metcalf, Thomas A.,Endoma-Arias, Mary Ann A.,MacH, Pavel,Hudlicky, Tomas
experimental part, p. 4407 - 4416 (2012/07/14)
A series of ortho-, meta-, and para- halogen-substituted methyl benzoate esters was subjected to enzymatic dihydroxylation via the whole-cell fermentation with E. coli JM109 (pDTG601A). Only ortho-substituted benzoates were metabolized. Methyl 2-fluorobenzoate yielded one diol regioselectively whereas methyl 2-chloro-, methyl 2-bromo- and methyl 2-iodobenzoates each yielded a mixture of regioisomers. Absolute stereochemistry was determined for all new metabolites. Computational analysis of these results and a possible rationale for the regioselectivity of the enzymatic dihydroxylation is advanced.
