Synthesis of cytotoxic cembranolide analogues via acid-induced opening of oxiranes

A large series of analogues of Eunicea cembranolides 1–3 were synthesized with the purpose of evaluating their cytotoxicity against 60 human cancer cell-lines. Most of the analogues were as active as the lead compounds and a few displayed increased cytotoxicity. Their syntheses were based on the specific reactivity and stereochemistry of the epoxide substructure and involved highly regio- and diastereoselective acid-induced chemical transformations.