Tetrahedron letters

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

T Shinada, Y Yoshida, Y Ohfune

Index: Shinada, Tetsuro; Yoshida, Yasutaka; Ohfune, Yasufumi Tetrahedron Letters, 1998 , vol. 39, # 33 p. 6027 - 6028

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Citation Number: 25

Abstract

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.