Heterocycles. X. Syntheses and Absolute Configurations of a Chiral Naphthoquinone Epoxide and Chiral Naphtho [1,2-c] isocoumarins
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概要
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The (+)-naphthoquinone epoxide (2) has been obtained by the phase-transfer chiral epoxidation of the naphthoquinone (1). Reduction of (+)-2 with sodium borohydride gives the (-)-cis-epoxyhydroxy ketone (3) and (-)-trans-epoxyhydroxy ketone (4). Further reduction of (-)-3 affords the (-)-cis-lactone (5), (-)-trans-lactone (6) and (+)-cis-epoxydiol (7). Alumina-induced lactonization of (+)-7 yields (-)-6. The 2S, 3R configuration for (+)-2 is deduced from the circular dichroism spectrum. The configurations of the 4-hydroxyl groups in (-)-3 and (-)-4 are determined by the Horeau's method.
- 公益社団法人日本薬学会の論文
- 1981-05-23
著者
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恩田 政行
School of Pharmaceutical Sciences, Kitasato University
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山口 裕子
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
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恩田 政行
Shenyang Pharmaceutical University
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針谷 義弘
北里大薬
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山口 裕子
School of Pharmaceutical Sciences, Kitasato University
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針谷 義弘
School of Pharmaceutical Sciences, Kitasato University
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