Studies On The Asymmetric Synthesis Of Curcuphenol, Heliannuol E And Aigialomycin D

This dissertation consisted of four parts:Chapter 1. The Reviews of Julia-Kocienshi OlefinationDescribed the mechanism, types and application of Julia-Kocienshi Olefination;Chapter 2. An enantioselective synthesis of (S)- and (R)-curcuphenolThe enantioselective synthesis of the phenolic sesquiterenses (S)- and(R)-curcuphenol is reported. The key step in this synthesis is asymmetric conjugate addition using the readily available optically pure sulfoxide as chiral auxiliary;Chapter 3. Studties on the Asymmetric Synthesis of Heliannuol EStudties on the asymmetric synthesis of Heliannuol E based on asymmetricconjugate addition using the readily available optically pure sulfoxide as chiral auxiliary;Chapter 4. Enantioselective total synthesis of Aigialomycin DAn 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.