Stereoselective Palladium-Catalyzed α-Arylation of 3-Aryl-1-Indanones : Total Synthesis of (+)-Pauciflorol F

Abstract

We have developed conditions for promoting highly efficient Pd-catalyzed α-arylation reactions of 3-aryl-1-indanones. Reactions employing the optimal catalytic system, involving Pd(OAc)2, X-Phos, and NaOtBu (1.1 equiv), are attended by decreased levels of formation of undesired products and they take place with high degrees of stereoselectivity. Additionally, this study has led to the first asymmetric synthesis of (+)-pauciflorol F in 5 steps, starting from the known acetophenone 33, in an overall 51% yield.