An alternative approach to synthesize pedamide,a key building block of pederin was described.Iodine-induced asymmetric heterocyclization was used as the key step to construct the skeleton,a tetrahydropyran ring with three chiral centers.Brown’s asymmetric allylation and Lewis acid-mediated allylation were investigated to introduce chains and chiral alcohols.Sharpless dihydroxylation decorated the side chain.And high optically pure target was obtained by removing the epimers formed in these reactions on column chromatography. An alternative approach to synthesize pedamide, a key building block of pederin was described. Iodine-induced asymmetric heterocyclization was used as the key step to construct the skeleton, a tetrahydropyran ring with three chiral centers. Brown’s asymmetric allylation and Lewis acid-mediated allylation were investigated to introduce chains and chiral alcohols. Sharpless dihydroxylation decorated the side chain. And high optically pure target was obtained by removing the epimers formed in these reactions on column chromatography.