高等学校化学学报 ›› 1987, Vol. 8 ›› Issue (7): 620.

• 研究简报 • 上一篇    下一篇

番石榴酸及其差向异构体的合成

聂新永, 王茜, 李裕林, 潘鑫复   

  1. 兰州大学有机化学研究所
  • 收稿日期:1986-01-05 出版日期:1987-07-24 发布日期:1987-07-24

Synthesis of Piscidic Acid and Its Epimer

Nie Xinyong, Wang Qian, Li Yulin, Pan Xinfu   

  1. Institute of Organic Chemistry, Lanzhou University, Lanzhou
  • Received:1986-01-05 Online:1987-07-24 Published:1987-07-24

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。

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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