化学学报 ›› 2012, Vol. 70 ›› Issue (12): 1367-1370.DOI: 10.6023/A1111101 上一篇    下一篇

研究论文

金催化分子间氧化炔合成5-(3-吲哚基)-噁唑天然产物

吴运东a, 彭莎a, 欧阳跃军b, 钱鹏程a, 何卫民a, 向建南a   

  1. a 湖南大学化学生物传感与计量学国家重点实验室 湖南大学化学化工学院 长沙 410082;
    b 怀化学院化学化工系 怀化 418000
  • 收稿日期:2011-11-10 修回日期:2012-04-19 出版日期:2012-06-28 发布日期:2012-04-20
  • 通讯作者: 何卫民, 向建南 E-mail:jnxiang@hnu.cn, wmhe82@hotmail.com
  • 基金资助:

    湖南省科技厅重点项目(No. 2009WK4005)、湖南省自然科学基金(No. 11JJ5008)和长沙市科技局重点项目(No. K082152-31)资助项目.

Total Synthesis of 5-(3-Indolyl)oxazole Natural Product via Gold-Catalyzed Intermolecular Alkyne Oxidation

Wu Yundonga, Peng Shaa, Ouyang Yuejunb, Qian Pengchenga, He Weimina, Xiang Jiannana   

  1. a State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University and College of Chemistry and Chemical Engineering, Changsha 410082;
    b Department of Chemistry and Chemical Engineering, Huaihua University, Huaihua 418000
  • Received:2011-11-10 Revised:2012-04-19 Online:2012-06-28 Published:2012-04-20
  • Supported by:

    Project supported by Department of Science and Technology Foundation of Hunan Province (No. 2009WK4005), Hunan Natural Science Foundation (No. 11JJ5008) and Changsha Science and Technology (No. K082152-31).

一价金配合物催化的研究, 为天然产物和生物活性分子的全合成开辟了新颖简捷的途径. 描述了一条简便直接、高效、环境友好的噁唑类天然产物的合成路线. 该路线以吲哚为原料, 经过碘化, N-Boc保护, Sonogashira偶联, 金催化成环反应(72%~88%), 脱保护等5步反应合成目标物. 关键反应是在金催化下8-甲基喹啉氮氧化物与炔(2)间产生α-羰基金卡宾中间体.

关键词: 金催化, 8-甲基喹啉氮氧化物, α-羰基金卡宾中间体, 噁唑, 吲哚

The recent development of new gold(I) catalytic methods has opened the door to the total synthesis of natural products and bioactive complex molecules. We describe a convenient, straightforward, efficient and environmentally benign protocol to synthesize the 5-(3-indolyl)oxazole. The new synthetic route was finished in five steps including iodization, N-Boc protection, Sonogashira cross-coupling, gold catalyzed reaction, deprotection using indole as the starting material. The key step was generation of α-oxo carbene via gold-catalyzed intermolecular oxidation of alkynes (2).

Key words: gold-catalysis, 8-methylquinoline N-oxide, α-oxo gold carbene, oxazole, indole