Total Synthesis of (±)-Plumbazeylanone, A Naphthoquinone Trimer from Plumbago zeylanica
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概要
- 論文の詳細を見る
We have investigated the total synthesis of (±)-plumbazeylanone (1), a naphthoquinone trimer based on two different pathways (I) and (II). The synthetic approach based on pathway (I) was not successful. However, the first synthesis of 1 from plumbagin (2a) was achieved by utilizing an unsymmetrical methylene-bridged dimer (20b), with a naphthoquinone unit and a naphthalene unit as a key intermediate, based on pathway (II), in 11 steps with an overall yield of 5.9%. This synthesis features regioselective nucleophilic 1,2-addition of the naphthyllithium reagent 4a to the C-1 position of naphthoquinone 20b, and the regio- and stereoselective dienone-phenol-type rearrangement of the 1,2-adduct 21b (1,2-migration of the naphthyl group to the C3-position on 21b) with 2 N-NaOH.
- 公益社団法人日本薬学会の論文
- 1999-02-15
著者
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TAKEYA Tetsuya
Showa College of Pharmaceutical Sciences
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TOBINAGA Seisho
Showa College of Pharmaceutical Sciences
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Takeya T
Showa Pharmaceutical University
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Tobinaga S
Showa Pharmaceutical University
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KAJIYAMA Manabu
Showa College of Pharmaceutical Sciences, Machida
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NAKAMURA Chikara
Showa College of Pharmaceutical Sciences, Machida
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Kajiyama Manabu
Showa College Of Pharmaceytical Sciences
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KAJIYAMA Manabu
Showa College of Pharmaceutical Sciences
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TAKEYA Tetsuya
Showa College of Pharmaceutical Sciences, Machida
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