Direct conversion of 1,2-diol into allyl sulfide. Regioselective transformation of (-)-quinic acid to (-)-shikimic acid

Article abstract of DOI:10.1016/S0040-4039(98)01239-8

Exo-1,2-diols 3 and 4 were efficiently converted into the corresponding allyl sulfides by means of tri-n-butylphosphine (Bu₃P) and diphenyl disulfide (PhS)₂. This method was applied to the introduction of a carbon- carbon double bond from diol 11 to give allyl sulfide 12 in a highly regioselective manner. The allyl sulfide 12 was transformed into (-)-shikimic acid (1) in four steps.