Synthesis of (+)-perillyl alcohol from (+)-limonene

(+)-Perillyl alcohol (1) has been synthesised in four steps and 39% overall yield from commercially available limonene oxide (4). The sequence features, as its key step, a palladium(0)-mediated transformation of a secondary allylic acetate (6) into its primary isomer (7). An application of (+)-perillyl alcohol (1) in a formal synthesis of naturally occurring (-)-mesembrine (2) and (-)-mesembranol was demonstrated. (C) 2014 Elsevier Ltd. All rights reserved.