高等学校化学学报

高等学校化学学报

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(±)-耳壳藻内酯的全合成研究(Ⅱ)

晏日安1, 苏镜娱2   

  1. 1. 暨南大学食品科学与工程系, 广州 510632; 2. 中山大学化学系, 广州 510275
  • 收稿日期:1900-01-01 修回日期:1900-01-01 出版日期:2006-06-10 发布日期:2006-06-10
  • 通讯作者: 晏日安

Total Synthesis of (±)Caulilide(Ⅱ)

YAN Ri-An1*, SU Jing-Yu2   

  1. 1. Department of Food Science and Engineering, Jinan University, Guangzhou 510632, China;
    2. Department of Chemistry, Zhongshan University, Guangzhou 510275, China
  • Received:1900-01-01 Revised:1900-01-01 Online:2006-06-10 Published:2006-06-10
  • Contact: YAN Ri-An

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被引次数

4

摘要： 以2,6,6-三甲基环己-2-烯-1,4-二酮为原料, 经选择性羰基保护、Wittig反应、脱保护基、 腈基水解和还原等5步反应合成了目标化合物, 总产率可达6.0%.

关键词: 耳壳藻内酯, 2,6,6-三甲基环己-2-烯-1,4-二酮, Wittig反应, 合成

Abstract: The Caulilide which shows a potent cytotoxicity was synthesized from 2,6,6trimethylcyclohex2ene1,4dione via selective ketalization, Wittig reaction, deprotection, hydrolysislactonization and reduction in 60% total yield, in which wittig reaction was the key step. The difficulty of this reaction came from the strong blocking effect, many reaction conditions were optimized, a better yield of this reaction was gained in 578%. The synthesis of caulilide was completed by reduction of a lactone with NaBH4, the crude product was separated by high performance liquid chromatography to give the target compound.

Key words: Caulilide, 2,6,6-Trimethylcyclohex-2-ene-1,4-dione, Wittig reaction, Synthesis

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