Stereoselective synthesis of the pheromone (R)-(-)-sulcatol, and its enantiopure (R)- and (S)-1-mono-, -1,1-di-, and -1,1,1-trifluoro analogues

The pheromone (R)-(-)-sulcatol (10a) and three of its enantiomeric mono- , di-, and trifluoro analogues 10b-d have been synthesized, in six steps and with good overall yields, starting from chiral (R)-2-methyl-5-[(4- methylphenyl)sulfinyl]pent-2-ene (1) and commercially available fluorinated or non-fluorinated acetates.