Stereoselective Synthesis of 3,5-Dihydroxypyrrolidin-2-ones Through a Photoinduced Multicomponent Reaction Followed by Dimerization

A photoinduced reaction between diazoketones, isocyanides and silanols, followed by aldol dimerization of the resulting multicomponent adduct, affords polyfunctionalized 3,5-dihydroxypyrrolidin-2-one heterocycles in a straightforward manner. Six new bonds and two quaternary carbons are formed in just two steps with this complexity-generating methodology. A high degree of stereoselectivity is also observed, as a result of the mild conditions employed. Moreover, the 3,5-dihydroxypyrrolidin-2-one scaffold can be found in two families of biologically relevant natural products, namely anchinopeptolides and eusynstyelamides. The synthetic approach herein described appears to be a very convenient route for the preparation of their analogues.