Divergent syntheses of the C1鈥揅14 and C15鈥揅25 fragments of amphidinolide C have been achieved. The synthesis of the C15鈥揅25 fragment featured cobalt-catalyzed modified Mukaiyama aerobic alkenol cyclization and sulfur-directed regiocontrolled Wacker oxidation of an internal alkene. The C1鈥揅14 fragment was established by alkenyllithium addition to an aldehyde followed by a challenging olefination of a highly inert C9 ketone.