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Acta Chimica Sinica ›› 2007, Vol. 65 ›› Issue (12): 1165-1171. Previous Articles     Next Articles

Original Articles

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-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