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Communication | Regular issue | Vol 34, No. 4, 1992, pp.651-656
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5965
Importance of the 2-Hydroxy Group for the Reactions of an Acetate of a Naturally Occurring Prohibitin, 4-Acetoxy-2-hydroxy-2H-1,4-benzoxazin-3(4H)-one, with Nucleophiles

Takayoshi Ishizaki, Yuichi Hashimoto, and Koichi Shudo*

*Faculty of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113, Japan

Abstract

A prohibitin, 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one, reacted readily with nucleophiles after 4-O-acetylation. The 2-hydroxy group is mandatory for the reactions. The plausible interpretation for the enhancing effect of the 2-hydroxy group on the benzoxazinone system's reactivity involves an acetal ring-opening and reclosure mechanism.