Iterative Synthesis of (Oligo)deoxypropionates via Zinc-Catalyzed Enantiospecific sp³−sp³ Cross-Coupling

Abstract

This group's recently reported mild zinc-catalyzed enantiospecific sp3-sp3 cross-coupling of lactic acid tert-butylester triflate with Grignard reagents was now applied to an iterative approach in the synthesis of a series of all four possible diastereomers of the shown trideoxypropionate. Oligodeoxypropionate structures are a common motif in a large number of biologically relevant natural products of polyketide origin thus making our approach a versatile tool in their synthesis.