Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd0Catalyzed Asymmetric C(sp3)H Activation [component]

A divergent enantioselective synthesis of (nor)illudalane sesquiterpenes was designed by using a Pd 0catalyzed asymmetric C(sp 3 )−H arylation as a key step to control the isolated, highly symmetric quaternary stereocenter of the target molecules. A matched combination of chiral substrate and catalyst proved optimal to reach good levels of stereoselectivity. This approach enabled the synthesis of three (nor)illudalanes, including (S)-deliquinone and (S)-russujaponol F, which are synthesized for
more » ... are synthesized for the first time in enantioenriched form.
doi:10.1021/acs.orglett.8b04086.s001 fatcat:eeytobakjjh2rcxyiizsrxw44e