Synthesis of a quaternary polyprenyl ammonium salt

Abstract

Reaction of primary C55-allylic alcohol moraprenol (WT 3C7-9-OH, a polyprenol from mulberry leaves) with triethylamine in the presence of phosphorus oxychloride leads to a quaternary ammonium chloride with a good yield (72%) and high cis-stereoselectivity of the terminal isoprene unit. Cationic polyprenyl derivatives may be useful for transfection and immunological studies.