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2012 , Vol. 32 >Issue 9: 1749 - 1752

DOI: https://doi.org/10.6023/cjoc1201042

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
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  • 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

  网络出版日期: 2012-03-30

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

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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
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  • State Key Laboratory Cultivation Base of Natural Gas Conversion, Ningxia University, Yinchuan 750021

Received date: 2012-01-04

  Revised date: 2012-05-11

  Online 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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摘要

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

本文引用格式

杨金会 , 落俊山 , 郭冬冬 , 黄文倩 . (±)-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[J]. 有机化学, 2012 , 32(9) : 1749 -1752 . DOI: 10.6023/cjoc1201042

Abstract

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

参考文献

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