My laboratory explores new strategies to directly transform alkenes and arenes for streamlining bioactive small molecule synthesis. This seminar will cover three themes representative of our research program: 1) oxidative Rh(III)/(IV)/(II)-catalyzed C–H functionalization en-route to benzylisoquinoline alkaloids, an approach distinct from conventional Rh(III) catalysis; 2) synergistic Brønsted acid/Lewis acid catalyzed Friedel–Crafts alkylations enabling direct reactions with unactivated, non-benzylic/allylic/propargylic alcohols; 3) total synthesis of eudemanolide natural products.