A stereocontrolled synthesis of , the C(10)-C(25) component of amphidinolide C (), has been efficiently achieved. Reaction of the dithiane component with nonracemic bis(epoxide) directly affords functionalized 2,5--disubstituted tetrahydrofuran . Propargylation is highly diastereoselective for the formation of the desired C(12)-C(13) stereochemistry, and the resulting terminal alkyne is utilized for a regioselective -silylstannylation. A general strategy is illustrated for sequential replacement of stannyl and silyl substituents of the trisubstituted alkene to yield ()-alkenyl iodide .
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