47(P03) 三置換オレフィンの立体選択的構築を鍵反応とした生理活性を有するジテルペン類の全合成(ポスター発表の部)

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Schizostatin (1) and plaunotol (2) are biologically active diterpenes possessing functionalized tri-substituted olefins. We synthesized 1, 2 and their derivatives using stereoselective constructions of tri-substituted olefin moiety. Schizostatin (1) has been isolated from Schizophyllum commune Fr. (SANK17785) as a potent and selective inhibitor of squalene synthase. Its structure has been determined using spectroscopic methods: the compound has a trans-dicarboxylic acid moiety. Total synthesis of schizostatin (1) was achieved by the highly regioselective and stereoselective coupling reaction of an allylic bromide with a barium reagent. The Z-isomer 17 was also prepared using the stereoselective syn-addition of an organocopper reagent to acetylenedicarboxylate. Plaunotol (2), which is a known antiulcer drug, is the most important component of Plau noi, a Thai folk medicine. Recently, it has also been reported that plaunotol shows antibacterial activities against Hericobactor pylori. We developed a practical and highly stereoselective synthesis of plaunotol (2) and its thiourea derivatives 28, 30 and 32, via the Z-selective Wittig reaction using α-acetal ketone 18 and phosphonium salt 19. Also their antibacterial activity against H. pylori are described.
天然有機化合物討論会の論文
1999-09-01