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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (8): 705-710. 上一篇    下一篇

研究论文

利用甾体皂甙元氧化降解废弃物(R)-4-甲基-δ-戊内酯合成松叶蜂主要性信息素(2S,3S,7S)-3,7-二甲基-2-十五醇乙酸酯和丙酸酯

王子坤1, 田伟生*,2, 潘鑫复1   

  1. (1兰州大学化学化工学院功能有机分子化学国家重点实验室 兰州 730000)
    (2中国科学院上海有机化学研究所资源化学与甾体化学实验室 上海 200032)
  • 投稿日期:2007-01-04 修回日期:2007-03-21 发布日期:2007-04-28
  • 通讯作者: 田伟生

Practical Synthesis of the Main Sex Pheromones of Pine Sawflies (2S,3S,7S)-3,7-Dimethylpentadecan-2-ol Esters by Utilizing (R)-4-Methyl-δ-Valerolactone Obtained from the Industrial Waste

WANG Zi-Kun1; TIAN Wei-Sheng*,2; PAN Xin-Fu1   

  1. (1 Department of Chemistry and State Key Laboratory of Applied Organic Chemistry, Lanzhou Uni-versity, Lanzhou 730000)
    (2 Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghhai 200032)
  • Received:2007-01-04 Revised:2007-03-21 Published:2007-04-28
  • Contact: TIAN Wei-Sheng

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首次利用甾体皂甙元氧化降解废弃物(R)-4-甲基-δ-戊内酯合成了松叶蜂性信息素(2S,3S,7S)-3,7-二甲基-2-十五醇乙酸酯(2)和丙酸酯(3). 甾体皂甙元氧化降解废弃物(R)-4-甲基-δ-戊内酯首先被转化成为性质稳定易保存的(R)-5-溴-4-甲基戊酸甲酯(5), 化合物5经过偶联、还原、溴代、环氧加成开环和酰化反应给出目标分子. 本研究结果不仅为松叶蜂性信息素化合物2和3提供了一个简洁有效的合成方法, 同时也丰富了资源化学(即基于资源性化合物合理利用的有机合成化学)的内涵.

关键词: 松叶蜂性信息素, (R)-4-甲基-δ-戊内酯, (R)-5-溴-4-甲基戊酸甲酯, 资源化学

The synthesis of the sex pheromones of pine sawflies (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate (2) and its propionate (3) by utilizing the industrial waste, (R)-4-methyl-δ-valerolactone in the degradation of steroidal sapogenin was first reported in this paper. (R)-4-Methyl-δ-valerolactone was transformed into (R)-methyl 5-bromo-4-methylpentanoate (5) which is a stable and easily reserved reagent. 5 then underwent a series of reaction involving coupling, reduction, bromination and addition to epoxide to give target molecules 2 and 3. This research result not only provides a concise synthetic method for (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate (2) and propionate (3), but also enrichs the connotation of resource chemistry (the organic synthetic chemistry based on the rational utilization of resource compounds).

Key words: sex pheromones of pine sawflies, (R)-4-methyl-δ-valerolactone, (R)-methyl 5-bromo-4- methylpentanoate, resource chemistry