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Communication | Special issue | Vol 99, No. 1, 2019, pp.126-133
Published online, 28th November, 2018
DOI: 10.3987/COM-18-S(F)50
Acetal Elimination Reaction Accompanied with Regioselective Ring Opening of 1,4-Bisacetal-1,4-epoxy-1,4-dihydronaphthalenes

Yoshinari Sawama,* Takahiro Kawajiri, Yuta Yamamoto, Yuko Shishido, Ryota Goto, and Hironao Sajiki*

*Laboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan

Abstract

1,4-Epoxy-1,4-dihydronaphthalenes are useful precursors to synthesize 1-naphthols by an acid-catalyzed ring opening of their 1,4-epoxy moieties. 1-Acetal-substituted 1,4-epoxy-1,4-dihydronaphthalene was also converted to 1-naphthol via the unique iron-catalyzed ring opening of the 1,4-epoxy moiety followed by the elimination of the acetal moiety. The present method could be applied to the regioselective syntheses of highly-functionalized 4-formyl-1-naphthols from the unsymmetrical 1,4-bisacetal-substituted 1,4-epoxy-1,4-dihydronaphthalenes.