| 番石榴酸及其差向异构体的合成 |
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| 引用本文： | 聂新永,王茜,李裕林,潘鑫复.番石榴酸及其差向异构体的合成[J].高等学校化学学报,1987,8(7):620. |
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| 作者姓名： | 聂新永 王茜 李裕林 潘鑫复 |
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| 作者单位： | 兰州大学有机化学研究所 |
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| 摘 要： | 番石榴酸(Piscidicacid) 8 是从Piscidacrgthrina中分离得到的一种水溶性化合物,1948年W.Bridge等证明其结构为对羟基苄基酒石酸,1971年T.Yoshihara等确定其绝对构型为(2R,3S),1981年发现它具有明显的药理作用。
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| 收稿时间： | 1986-01-05 |
Synthesis of Piscidic Acid and Its Epimer |
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| Nie Xinyong,Wang Qian,Li Yulin,Pan Xinfu.Synthesis of Piscidic Acid and Its Epimer[J].Chemical Research In Chinese Universities,1987,8(7):620. |
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| Authors: | Nie Xinyong Wang Qian Li Yulin Pan Xinfu |
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| Institution: | Institute of Organic Chemistry, Lanzhou University, Lanzhou |
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| Abstract: | The (2R,3R) -dimethyl tartrate acetonide(1) was reacted with p-benzyloxy-benzyl bromide(2) at-78℃ in the presence of LDAto convert successfully(1) to dimethyl(2R,3R)-2-benzyloxybenzyl-tartrate acetonide (3). The dimethyl (2R, 3R)-2-benzyloxybenzyl-tartrate acetonide (3) was treated with CH3ONa and the major product was the 81% enantiomerically pure erythro-isomer (5). The benzyl and acetonide groups of dimethyl (2R,3S)-2-benzyloxybenzyl tartrate acetonide (5) and dimethyl (2R,3R)-2-benzyloxybenzyl tartrate acetonite (3) were removed, respectively, by treating with CH3CO2H-HCl-H,O(2:1:1) for 1.5 hrs., and hydrolyzing with 0.5N NaOH. The piscidic acid (8) and its epimer (7) were obtained successfully. |
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