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Updated: Jun 1, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Synthesis of biologically active (-)-dehydroiso-β-lapachone and the determination of its absolute configuration
Tetsutaro Kimachi1, Eri Torii, Yusuke Kobayashi
1School of Pharmaceutical Sciences, Mukogawa Women's University, 11–68 Koshien Kyubancho, Nishinomiya, Hyogo, Japan. tkimachi@mukogawa-u.ac.jp
Abstract:
Synthesis of dehydoriso-β-lapachone (1) in both racemic and enantioenriched forms is achieved starting from reduced naphthoquinone equivalents. As for the synthesis of enantioenriched dehydroiso-β-lapachone, introduction of the asymmetric center was carried out by catalytic asymmetric epoxidation of the unfunctionalized trisubstituted olefin using Shi epoxidation diketal catalyst. The construction of isopropenylfurano-1,2-(β)-naphthoquinone was carried out by acidic ring-opening reaction of the epoxynaphthalene and the following diammonium cerium(IV) nitrate (CAN) oxidation. The absolute configuration of naturally occurring (-)-dehydroiso-β-lapachone was finally determined as (R) by comparing the measured optical rotation value of the synthetic (R)-dehydroiso-β-lapachone.
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