Stereoselective synthesis of the C1–C8 subunit of peloruside A

Abstract

Two routes to the C1–C8 subunit of peloruside A are disclosed. The first route involving 14 steps exploits Krische's 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 Jacobsen's hydrolytic kinetic resolution of an epoxide and Sharpless' asymmetric dihydroxylation reaction as the key steps.