105(P32) 苔類より得られた大環状ビスビベンジル構造を有するプラジオチン類の合成研究(ポスター発表の部)
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概要
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Macrocyclic Bis(bibenzyls) are plant metabolites occurring exclusively in liverworts, and over 30 congeners have been isolated so far. Their unique structures and diversity of their biological activities have attracted much attention. They may be categorized into two structural types 1 and 2, which consist of macrocyclic rings linked via two biphenyl ether bonds, and one biphenyl and one biaryl bonds, respectively, presumably derived by oxidative couplings of open chain bis(bibenzyls). In particular, plagiochin A (1), belonging to type 2 macrocyclic bis(bibenzyls), exhibits potent neurotrophic activity in culture of fetal rat cerebral hemisphere. As a part of studies on macrocyclic bis(bibenzyls), we have investigated synthesis of plagiochin D (4) based on two different strategies for macrocyclization. The first synthetic effort is a macrocyclization between benzylic carbons after preparation of biaryl unit. The A and C unit 12 was readily obtained by Ullmann coupling between 9 and 10, whereas Pd(0) catalyzed Suzuki reaction between 14 and 16 gave rise to the B and D biaryl unit 17, quantitatively. The units 12 and 17 were combined by Wadsworth-Emmons reaction to yield 18, which failed to be cyclized even by using several ways successively applied for the macrocyclization of type 1 macrocyclic bis(bibenzyls). The displacement of the dibromide in 19 with Na_2S realized the cyclization through a thioether bond giving rise to 20, which was treated with in situ generated benzyne followed by reduction to afford plagiochin D (4) in poor yield. The second strategy involves not only the formation of biaryl bond and but also macrocyclization between B and D rings using transition metal catalyst. The dibromoperrottetin E derivative 26 was readily prepared starting from m-anisaldehyde (13) by procedures essentially similar to those used for the first strategy. After several attempts for cross coupling of 26, Kelly-Still protocol [(Me_3Sn)_2, Pd(PPh_3)_4, toluene, 120℃] was found to realize the cross coupling to afford plagiochin dimethoxymethyl ether (4a) in 17% yield. In addition, the monotrimethylstannic derivative 27 could be converted to 4a under the Still condition in 15% yield.
- 天然有機化合物討論会の論文
- 1998-08-31
著者
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中村 和彦
慶大理工
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福山 愛保
徳島文理大・薬
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八十 秀行
徳島文理大・薬
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中村 和彦
徳島文理大・薬
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児玉 三明
徳島文理大・薬
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福山 愛保
徳島文理大薬
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児玉 三明
徳島文理大薬
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Kodama M
Otsuka Pharmaceutical Co. Ltd.
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