Synthesis of Biologically Active (−)-Dehydroiso-β-lapachone and the Determination of Its Absolute Configuration

概要

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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.
公益社団法人　日本薬学会の論文