Synlett

Syntheses of gabosine A, B, D, and E from allyl sulfide derived from (-)-quinic acid

T Shinada, T Fuji, Y Ohtani, Y Yoshida, Y Ohfune

Index: Shinada, Tetsuro; Fuji, Toshiyuki; Ohtani, Yasuhiro; Yoshida, Yasutaka; Ohfune, Yasufumi Synlett, 2002 , # 8 p. 1341 - 1343

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Citation Number: 19

Abstract

Abstract An efficient conversion of allyl sulfide 6 prepared from (-)-quinic acid (5) to gabosines was achieved by a series of sequential reactions: i) Mislow-Evans rearrangement, ii) SeO 2 oxidation, iii) conjugate addition of sodium hydroxide or sodium acetate, and iv) elimination of the methoxymethyloxy group.