| A one-pot oxidative [3,3]-sigmatropic rearrangement/Friedel--Crafts arylation reaction was developed to access enantioenriched benzhydryl compounds. This powerful fragment coupling reaction forged two carbon--carbon bonds, and set two stereogenic centers. The utility of this methodology was highlighted in the concise, stereoselective synthesis of six lignan natural products in eight steps or less with yields ranging from 16% to 56%.;An undesired by-product isolated during initial studies towards the lignan natural products served as inspiration for developing a new method for the synthesis of indanes, an important structural motif in many bioactive compounds. The Bronsted acid-catalyzed fragment coupling of allylsilanes and benzyl alcohols synthesize complex, yet diverse architectures from simple building blocks, and allow rapid access to large compound libraries for biological evaluation. Efforts to expand this methodology to the synthesis of other fused ring systems such as tetralins and chromanes are underway. |
