An enantioselective total synthesis of (-)-cladospolide B was described.The key steps in this synthesis include (a) a Sharpless asymmetric dihydroxylation to elaborate syn diol at C-4 and C-5 positions;(b) a Mitsunobu esterification to reverse the configuration at C-11 from (S) to (R);and (c) a ring-closing metathesis to access the 12-membered macrocyclic ring.