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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (1): 32-36. 上一篇    下一篇

研究论文

光学活性化合物多羟基庚酸乙酯的合成

王进欣1,2, 何玲1, 尤启冬*,1, 李灜*,2   

  1. (1中国药科大学药学院 南京 210009)
    (2兰州大学功能有机分子化学国家重点实验室 兰州 730000)
  • 投稿日期:2006-03-08 修回日期:2006-04-10 发布日期:2007-01-14
  • 通讯作者: 尤启冬

The Synthesis of the Optically Active Ethyl Polyhydroxy Heptanoate

WANG Jin-Xin1,2; HE Ling1; YOU Qi-Dong*,1; LI Ying*,2   

  1. (1 School of Pharmacy, China Pharmaceutical University, Nanjing 210009)
    (2 State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000)
  • Received:2006-03-08 Revised:2006-04-10 Published:2007-01-14

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以不对称环氧化和双羟化反应为构筑手性碳的关键步骤, 首次合成了(＋)-(2R,3S,4S,5S)-6-甲基-4,5-环氧-2,3-二羟基-庚酸乙酯(5)和(－)-(2R,3S,4R,5S)-6-甲基-2,3,4,5-四羟基-庚酸乙酯(11). 找到一条适宜于该类化合物合成的简便有效且立体选择性好的合成路线. 初步生物活性测试表明, 化合物5, 11对HL60细胞具有抑制活性.

关键词: (＋)-(2R,3S,4S,5S)-6-甲基-4,5-环氧-2,3-二羟基-庚酸乙酯, (－)-(2R,3S,4R,5S)-6-甲基-2,3,4,5-四羟基-庚酸乙酯, 不对称双羟化反应, 抗肿瘤活性

The first synthesis of ethyl (＋)-(2R,3S,4S,5S)-4,5-epoxy-2,3-dihydroxy-6-methyl heptanoate (5) and ethyl (－)-(2R,3S,4R,5S)-2,3,4,5-tetrahydroxy-6-methyl heptanoate (11) was achieved and the key steps involved the construction of chiral carbon centers by the asymmetric epoxidation and dihydroxylation. This efficiently concise strategy has better stereochemistry and is adapted to the synthesis of polyhydroxyl fatty acid analogues. The primary tests of compounds 5 and 11 showed better inhibitory activities against HL60 cell line.

Key words: (＋)-(2R,3S,4S,5S)-4,5-epoxy-2,3-dihydroxy-6-methyl heptanoate, ethyl (－)-(2R,3S,4R, 5S)-2,3,4,5-tetrahydroxy-6-methyl heptanoate, asymmetric dihydroxylation, antitumor activity