Catalytic Enantioselective Silylation of Acyclic and Cyclic Triols: Application to Total Syntheses of Cleroindicins D, F, and C


  • Financial support was provided by the NIH (GM-57212) and Z.Y. acknowledges support as a LaMattina Graduate Fellow. We are grateful to Dr. Yu Zhao and Jason Rodrigo (Boston College) for experimental assistance and helpful discussions. Mass spectrometry facilities at Boston College are supported by the NSF (DBI-0619576).


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Pick one out of three: Acyclic and cyclic 1,2,3-triols are silylated with exceptional site- and enantioselectivity by a small-molecule catalyst to afford silyl ethers having a neighboring diol moiety. The new process is applied to the enantioselective total syntheses of three cleroindicins, natural products isolated from a plant used in China to battle malaria and rheumatism.