[reaction: see text] A simple procedure for the cleavage of triethylsilyl (TES) ethers in the presence of 10 wt % Pd/C in methanol or 95% ethanol is reported. This method allows selective removal of alkyl TES ethers in the presence of aromatic TES ethers or tert-butyldimethylsilyl (TBS) protecting groups.

We have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syn-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C.