Synthetic studies of microtubule stabilizing agent peloruside A: an asymmetric synthesis of C10C24 segment

An asymmetric synthesis of the C10C24 fragment of the potent antitumor macrolide, peloruside A is described. All three stereogenic centers have been enantioselectively constructed utilizing Evans alkylation, Brown asymmetric allylboration, and a substrate controlled epoxide formation. Other key reactions involved Grubbsʹs ring-closing olefin metathesis and Andoʹs Z-selective olefination reaction.