An asymmetric synthesis of 7-hydroxy-9-propylnonenolide (herbarumin III)

An asymmetric synthesis of herbarumin III has been developed using (R)-cyclohexylidene glyceraldehyde 1 as the chiral template. The key steps of the synthesis were the enantioselective preparation of the required homoallylic alcohol from 1, an asymmetric dihydroxylation, and a ring-closing metathesis reaction for the macrolactonization.