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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (12): 1165-1171. 上一篇    下一篇

研究论文

利用工业废弃物中获得的(R)-5-甲基-δ-戊酸内酯为原料合成(2R,6R)-2,6,10-三甲基十一醇

李涛1, 黄贤贵2, 林静容2, 金荣华2, 田伟生*,1,2   

  1. (1中国科学院上海有机化学研究所 上海 200032)
    (2上海师范大学资源化学室验室 上海 200234)
  • 投稿日期:2006-04-26 修回日期:2007-01-29 发布日期:2007-06-28
  • 通讯作者: 田伟生

Total Synthesis of (2R,6R)-2,6,10-Trimethylundecan-1-ol with (R)-5-Methyl-δ-valerolactone from the Industrial Waste

LI Tao1; HUANG Xian-Gui2; LIN Jing-Rong2; JIN Rong-Hua2; TIAN Wei-Sheng*,1,2   

  1. (1 Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
    (2 Laboyatory of Resource Chemistry, Shanghai Normal University, Shanghai 200234)
  • Received:2006-04-26 Revised:2007-01-29 Published:2007-06-28
  • Contact: TIAN Wei-Sheng

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(2R,6R)-2,6,10-三甲基十一醇(1)是维生素E、维生素K和植醇的基本结构单元. 利用从甾体皂甙元氧化降解产生的工业废弃物中所获得的手性化合物(R)-5-甲基-δ-戊酸内酯(6), 先将其转化成为化学性质稳定的(4R)-甲基-5-甲氧甲氧基戊酸甲酯(7), 再经十二步反应, 以14.1%的总收率合成得到了目标化合物(2R,6R)-2,6,10-三甲基十一醇(1).

关键词: 全合成, 维生素E侧链, (2R,6R)-2,6,10-三甲基十一醇

(2R,6R)-2,6,10-Trimethylundecan-1-ol (1), which is a basic structural unit of Vitamin E, Vitamin K and phytol, was synthesized starting from methyl (4R)-methyl-5-methoxymethoxyl valerate (7) in 12 steps and in 14.1% overall yield. The later was prepared from (R)-5-methyl-δ-valerolactone (6), a chiral building block obtained from the industrial waste in the degradation of steroidal sapogenin.

Key words: total synthesis, vitamin E side chain, (2R,6R)-2,6,10-trimethylundecan-1-ol