First total synthesis of natural aplyolides B and D, ichthyotoxic macrolides isolated from the skin of the marine mollusk Aplysia depilans

A convergent pathway is described for the synthesis of the marine macrolides aplyolides B (2) and D (3). Stereoselective preparation of a key fragment was achieved by Sharpless asymmetric dihydroxylation of eneyne 10.