高等学校化学学报

高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (7): 1219.

• 论文 • 上一篇    下一篇

(±)-19-去甲基-4(18),8,11,13-四烯-松香烷-7-酮的全合成

别平彦, 张成路, 彭宣嘉, 陈博, 杨毅, 潘鑫复   

  1. 兰州大学化学系, 应用有机化学国家重点实验室, 兰州 730000
  • 收稿日期:2002-07-03 出版日期:2003-07-24 发布日期:2003-07-24
  • 通讯作者: 潘鑫复(1937年出生),男,教授,博士生导师,主要从事有机合成和天然产物化学合成研究.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

Total Synthesis of (±)-19-Norabieta-4(18),8,11,13-tetraen-7-one

BIE Ping-Yan, ZHANG Cheng-Lu, PENG Xuan-Jia, CHEN Bo, YANG Yi, PAN Xin-Fu   

  1. Department of Chemistry, National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2002-07-03 Online:2003-07-24 Published:2003-07-24

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摘要： 以间异丙基溴苯1为起始原料,通过进攻环氧乙烷及溴代两步制得溴化物3.溴化物3与Hagemann′s酯发生偶联反应,水解后生成偶联产物5.再以路易斯酸BF3·Et2O催化化合物5进行分子内环化为关键步骤得到反式稠合中间体6,最后通过与三苯基膦碘甲烷季盐发生Wittig反应及氧化,合成了(±)-19-去甲基-4(18),8,11,13-四烯-松香烷-7-酮[19-nor-abieta-4(18),8,11,13-tetraen-7-one](8).

关键词: 三环二萜, 全合成, 天然产物

Abstract: (±)-19-Norabieta-4(18),8,11,13-tetraen-7-one(8) was first synthesized starting from m-isopropylbromobenzene(1). After bromination of alcohol(2), coupling reaction of bromide(3) with Hagemann′s ester in the presence of t-BuOK and hydrolysis of compound(4) with KOH, compound (5) was obtained in a high yield. Intramolecular cyclization of coupling compound(5) with BF3·Et2O afforded a trans-fused key intermediate(6). After structural modification by Wittig reaction with Ph3P +CH3I-and oxidation with CrO2, the target molecule was obtained in a good yield.

Key words: Tricyclic diterpene, Total synthesis, Natural product

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