高等学校化学学报

高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (6): 1019.

• 论文 • 上一篇    下一篇

(±)-12-乙基-13-甲氧基-8,11,13-罗汉松三烯-7-酮和(±)-12-乙基-13-甲氧基-8,11,13-罗汉松三烯的全合成

张成路1,2, 别平彦1, 彭宣嘉1, 潘鑫复1   

  1. 1. 兰州大学化学系, 应用有机化学国家重点实验室, 兰州 730000;
    2. 辽宁师范大学化学系, 大连 116029
  • 收稿日期:2002-05-28 出版日期:2003-06-24 发布日期:2003-06-24
  • 通讯作者: 潘鑫复(1937年出生),男,教授,博士生导师,主要从事天然产物的合成研究.E-mail:panxf@lzu.edu.cn E-mail:panxf@lzu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:20172023)资助d:\PDF\.pdf

Total Synthesis of (±)-Nimbonone and (±)-12-Ethyl-13-methoxy-8,11,13-podocarpatriene

ZHANG Cheng-Lu1,2, BIE Ping-Yan1, PENG Xuan-Jia1, PAN Xin-Fu1   

  1. 1. Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China;
    2. Department of Chemistry, Liaoning Normal University, Dalian 116029, China
  • Received:2002-05-28 Online:2003-06-24 Published:2003-06-24

PDF (PC)

摘要： 以α-环柠檬醛(1)为A环合成子,以季盐(2)为C环合成子,经缩合及分子内环化反应得到关键中间体(5).为引入乙基,进行了Friedel-Crafts反应和脱氧反应等,共经7步反应得到了(±)-12-乙基-13-甲氧基-8,11,13-罗汉松三烯-7-酮[(±)-nimbonone](9)及(±)-12-乙基-13-甲氧基-8,11,13-罗汉松三烯(10).

关键词: 全合成, 三环二萜, (±, )-12-乙基-13-甲氧基-8, 11, 13-罗汉松三烯-7-酮

Abstract: BYUsing α-cyclocitral(1) as the A ring synthon, and triphenyl phosphonium chloride(2) as the C ring synthon, the keYINtermediate 5 was obtained after the condensation and intracyclization reactions. In order to introduce the ethyl substituent, Fiedel-Crafts acetylation had been first employed to synthesize compound 6, and then the carbonyl group in compound 6 was protected with 1,2-ethanedithiol to afford compound 7. Compound 7 was oxidized to afford compound 8. Desulfurization of compounds 7 and 8 with Raney Ni gave the desired products (±)-nimbonone (9) and (±)-12-ethyl-13-methoxy-8,11,13-podocarpatriene (10) respectively.

Key words: Total synthesis, Tricyclic diterpenes, (±)-Nimbonone

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