A Three-Step Synthesis of an Alkyne Containing Farnesyl Derivative

Farnesylation is a key protein modification for cellular signaling that is unregulated in cancer patients. The goal here is to synthesize an alkyne-containing farnesyl mimic that will allow for the targeting of farnesylated proteins. First, farnesol was THP protected using dihydropyran and PPTs. The THP protected farnesol was then oxidized using SeO2 and tert-butyl hydrogen peroxide and purified using column chromatography. The resulting alcohol was then converted to an alkyne containing ether upon treatment with NaH and BrCHCH2CCH. To make the reaction greener, t-Bu-OOH, a harmful solvent used in this synthesis, is to be replaced with an alternative solvent such as hydroperoxide 1, 1-dimethylethyl, or Hydroperoxide-d.