17: Investigation of asymmetric ring-opening reactions from Meso 1,4-Dihydro-1,4:4a,9a-diepoxyanthracene-9,10-diones for the enantioselective synthesis of epoxyanthraquinol natural products

Abstract: Cervicarcin and mensacarin represent two highly oxygenated anthracenyl-type epoxyquinol polyketides that have yet to succumb to total synthesis. In preparation for planned stereo- and regio-controlled elaborations of these complex bioactive natural product targets, our ongoing investigation of asymmetric ring-opening (ARO) reactions from meso 1,4-dihydro-1,4:4a,9a-diepoxyanthracene-9,10-diones (and related oxanaphtho[b]norbornadienes) will be presented. Unoptimized routes to both cis and trans diastereoisomers of the key meso substrates have been established and an initial study of a Lautens-type ARO reaction from the trans isomer has revealed that conversion to the expected chiral fused cyclohexenol is achievable, at least in low yield.