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2012 , Vol. 70 >Issue 12: 1367 - 1370

DOI: https://doi.org/10.6023/A1111101

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 ,
  • 彭莎 ,
  • 欧阳跃军 ,
  • 钱鹏程 ,
  • 何卫民 ,
  • 向建南
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  • 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

  网络出版日期: 2012-04-20

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.

收起

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

  • Wu Yundong ,
  • Peng Sha ,
  • Ouyang Yuejun ,
  • Qian Pengcheng ,
  • He Weimin ,
  • Xiang Jiannan
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  • 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 date: 2011-11-10

  Revised date: 2012-04-19

  Online 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).

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摘要

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

本文引用格式

吴运东 , 彭莎 , 欧阳跃军 , 钱鹏程 , 何卫民 , 向建南 . 金催化分子间氧化炔合成5-(3-吲哚基)-噁唑天然产物[J]. 化学学报, 2012 , 70(12) : 1367 -1370 . DOI: 10.6023/A1111101

Abstract

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

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