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Short Paper | Special issue | Vol 99, No. 1, 2019, pp.625-632
Published online, 23rd July, 2018
DOI: 10.3987/COM-18-S(F)12
Lipase-Catalyzed Site-Selective Deacetylation of Sterically Hindered Naphthohydroquinone Diacetate and Its Application to the Synthesis of a Heterocyclic Natural Product

Riichi Hashimoto, Ayaka Sakakura, Kengo Hanaya, Shuhei Higashibayashi, and Takeshi Sugai*

*Department of Pharmaceutical Sciences, Faculty of Pharmacy, Keio University, 1-5-30 Shiba-Kouen, Minato-ku, Tokyo, Japan

Abstract

Lipase-catalyzed site-selective deacetylation of 2,5-dimethylnaphthalene-1,4-diol diacetate was examined. With Candida antarctica lipase B, the suppressing effect of a methyl substituent at the peri-position of the α-naphthyl ester over that at the ortho-position was significant. This site-selectivity was in contrast to that of chemical hydrolysis reported to date. From the resulting monoacetate, mansonone F, a physiologically active heterocyclic orthoquinone, was synthesized in 38% yield in as few as three steps.