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 BrCH_2­CH₂CCH. 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.