A convergent and stereoselective synthesis of the glycolipid components phthioceranic acid and hydroxyphthioceranic acid

Simply convergent: The polydeoxypropionates 1 and 2 are important constituents of the cell wall of Mycobacterium tuberculosis. Key steps in their total synthesis include two Suzuki-Miyaura cross-coupling reactions and two highly diastereoselective iridium-catalyzed hydrogenations. The trideoxypropionates employed as central building blocks were prepared by sequential oxy-Cope rearrangement, hydrogenation, and enolate methylation.