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An efficient, convergent approach for the total synthesis of aigialomycin D (1) is described. Key features of the synthetic strategy include (a) Sharpless asymmetric epoxidation reaction and selective opening 2,3-epoxy alcohol to elaborate the two hydroxy-bearing stereogenic centers at C5’and C6’ position; (b) Kocienski modified Julia protocol to construct the two E-configured double bonds; (c) Yamaguchi macrolactonization to acccess the 14-membered macrocyclic ring. |
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Keywords:Total synthesis, Titanium-assisted regioselective opening of 2,3-epoxy alcohol, Kocienski modified Julia coupling, Yamaguchi macrolactonization. |
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