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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (9): 1749-1752.DOI: 10.6023/cjoc1201042 上一篇    下一篇

研究简报

(±)-5,3'-二羟基-7,8-(2,2-二甲基吡喃)-4'-甲氧基黄烷酮的首次全合成

杨金会, 落俊山, 郭冬冬, 黄文倩   

  1. 宁夏大学天然气转化国家重点实验室培育基地 银川 750021
  • 收稿日期:2012-01-04 修回日期:2012-05-11 发布日期:2012-03-30
  • 通讯作者: 杨金会 E-mail:yang_jh@nxu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.20962016, 21162021)、教育部新世纪优秀人才支持计划(No.NCET-09-0860)、宁夏自然科学基金(No.NZ1006)资助项目

tal Synthesis of (±)-5,3'-Dihydroxy-4'-methoxy-6",6"-dimethyl-chromeno-(7,8,2",3")-flavanone

Yang Jinhui, Lao Junshan, Guo Dongdong, Huang Wenqian   

  1. State Key Laboratory Cultivation Base of Natural Gas Conversion, Ningxia University, Yinchuan 750021
  • Received:2012-01-04 Revised:2012-05-11 Published:2012-03-30
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos.20962016, 21162021), the Program for New Century Excellent Talents in University (No.NCET-09-0860) and the Natural Science Foundation of Ningxia Hui Autonomous Region (No.NZ1006)

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以廉价的异香草醛和2,4,6-三羟基苯乙酮为起始原料,经过C-异戊烯基化、环化、选择性的保护酚羟基、羟醛缩合、催化环化等步骤,脱保护基,以6.7%的总收率首次完成了天然吡喃型黄烷酮(±)-5,3'-二羟基-7,8-(2,2-二甲基吡喃)-4'-甲氧基黄烷酮的全合成.所有新化合物的结构都经过IR,1H NMR,MS,HRMS确认.

关键词: 5,3'-二羟基-7,8-(2,2-二甲基吡喃)-4'-甲氧基黄烷酮, 全合成, 苯并吡喃型黄烷酮

The total synthesis of (±)-5,3'-dihydroxy-4'-methoxy-6",6"-dimethyl-chromeno-(7,8,2",3")-flavanone was first achieved through C-prenylation, cyclization, selective protection of phenolic hydroxyl group, aldol condensation, cyclization and deprotection starting from cheap isovanillin and 2,4,6-trihydroxyacetophenone, with total yield 6.7%. All structures of new compounds were confirmed by IR,1H NMR, MS and HRMS techniques.

Key words: 5,3'-dihydroxy-4'-methoxy-6",6"-dimethylchromeno-(7,8,2",3")-flavanone, total synthesis, pyranoflavanone