A regiodivergent synthesis of ring A C-prenylflavones

(Chemical Equation Presented) Capitalizing on the use of orthogonal protecting groups and the development of a modified Robinson flavone synthesis that avoids harsh acidic conditions, a regioselective synthesis of 6- and 8-prenylflavones from the same prenylated disilylated phloracetophenone (9) has been developed, targeting cannflavin B (1d), the COX-inhibiting principle of marijuana, and its unnatural isomer isocannflavin B (1e) as model compounds.