Total Synthesis of the Polyketide Natural Product (-)-Pironetin and Studies Directed Toward the Total Synthesis of Iriomoteolide 1a

Polyketides are secondary metabolites with diverse structural scaffolds. The research summarized herein describes the biomimetic total synthesis of the polyketide (-)-pironetin utilizing iterative aldol additions of thiazolidinethiones to create five of the six total stereocenters of (-)-pironetin. This technology has also been applied to a convergent synthesis to the core of the polyketide iriomoteolide 1a.