Stereoselective synthesis of the C1–C8 subunit of peloruside A

Two routes to the C1–C8 subunit of peloruside A are disclosed. The first route involving 14 steps exploits Krischeʹs allylation, substrate controlled 1,3-asymmetric induction during bromohydrin formation from an alkene utilizing an intramolecular sulfinyl group as a nucleophile and Pummerer reaction as key steps. The second, shorter, scalable route (seven steps) exploits catalytic asymmetric reactions including Jacobsenʹs hydrolytic kinetic resolution of an epoxide and Sharplessʹ asymmetric dihydroxylation reaction as the key steps.