中华医学超声杂志

应用化学 ›› 2009, Vol. 26 ›› Issue (11): 1301-1304.

• 研究论文 • 上一篇    下一篇

3-羰基-10-去甲基-12-甲氧基-13-甲基罗汉松烷的全合成

张成路*,王利东,广东,申洪江,李元东,王杨   

  1. (辽宁省生物技术与分子药物研发重点实验室,辽宁师范大学化学化工学院 大连 116029)
  • 收稿日期:2008-10-20 修回日期:2009-04-08 出版日期:2009-11-10 发布日期:2009-11-10
  • 通讯作者: 张成路,男,教授; E-mail:zhangchenglu2208@sohu.com; 研究方向：天然产物合成

Total Synthesis of 3-Carbonyl-10-demethyl-12-methoxy-13-methylpodocarpene

ZHANG Cheng-Lu*, WANG Li-Dong, GUANG Dong, SHEN Hong-Jiang, LI Yuan-Dong, WANG Yang   

  1. (Liaoning Provincial key Laboratory of Biotechnology and Drug Discovery,Schoolof Chemistry
    and Chemical Engineering,Liaoning Normal Univeersity,Dalian 116029)
  • Received:2008-10-20 Revised:2009-04-08 Published:2009-11-10 Online:2009-11-10

PDF

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摘要：

以1，3-环己二酮为原料，经过甲基化反应和羰基保护构筑了A环合成子(5)。以邻甲基苯甲醚为原料，对位溴代、与环氧乙烷加成和进一步溴代等反应合成了C环合成子(9)。化合物5与9的格氏试剂偶联和关环反应完成目标产物3-羰基-10-去甲基-12-甲氧基-13-甲基罗汉松烷(11)的全合成。各中间体及目标产物结构均经红外光谱、核磁、质谱等表征，结果表明,成功实现了目标产物的合成。

关键词: 三环二萜, 罗汉松烷, 全合成

Abstract:

The A ring synthon 5 was synthesized from 1, 3-cyclohexanedione through methylation and carbonyl protection. The C ring synthon 9 was synthesized from 1-methoxy-2-methylbenzene by bromination, the addition of ethylene epoxide and further bromination. Compound 5 reacted with Grignard reagent of 9 and then performed cyclozation to afford the target molecule 11. All intermediates and target product were confirmed by IR, 1H NMR and HRMS. In conclusion, a simple synthetic route has been developed and the target molecule was successfully synthesized.

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