Synthesis of C11 to C21 polyol fragment of sekothrixide based on an iterative approach including iridium-catalyzed hydrosilylation of morpholine amides

Abstract An iterative approach to the synthesis of polyol fragments of polyketides is developed based on an iridium-catalyzed hydrosilylation of morpholine amides. Each round includes an aldol reaction using either morpholine amide or morpholine ketoamide and iridium-catalyzed hydrosilylation of the morpholine amide to give the new aldehyde, which is used for the next round. This strategy is successfully applied to the concise synthesis of the C11 to C21 polyol fragment of sekothrixide.