高等学校化学学报 ›› 2005, Vol. 26 ›› Issue (2): 259.

• 研究论文 • 上一篇    下一篇

天然产物(±)-Aiphanol的全合成研究

王小龙, 夏亚穆, 冯建鹏, 曹小平, 潘鑫复   

  1. 兰州大学化学化工学院, 功能有机分子化学国家重点实验室, 兰州 730000
  • 收稿日期:2003-11-27 出版日期:2005-02-10 发布日期:2005-02-10
  • 通讯作者: 曹小平(1957年出生),女,教授,博士生导师,主要从事天然产物的合成研究.E-mail:caoxplzu@163.com潘鑫复(1937年出生),男,教授,博士生导师,主要从事天然产物的合成研究.E-mail:panxf@lzu.edu.cn E-mail:panxf@lzu.edu.cn
  • 基金资助:

    国家自然科学群体基金(批准号:20021001);国家自然科学基金(批准号:20172023)资助

Total Synthesis of Natural Product (±)-Aiphanol

WANG Xiao-Long, XIA Ya-Mu, FENG Jian-Peng, CAO Xiao-Ping, PAN Xin-Fu   

  1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China
  • Received:2003-11-27 Online:2005-02-10 Published:2005-02-10

摘要: 以醛1和5为起始原料,经几步反应后用Ag2O偶联,得到含苯并二氧六环骨架的化合物7,化合物7经过选择性保护酚羟基,再用NaIO4/OsO4(cat.)氧化断裂双键,得到关键中间体9,化合物9和10经过Wittig-Horner反应,并用苯硫酚和AIBN实现了顺式双键向反式的转化,脱去保护基后完成了具有新颖结构的天然产物(±)-Aiphanol(12)的合成.

关键词: (±, )-Aiphanol, 二苯乙烯, 苯并二氧六环, Ag2O偶联, NaIO4/OsO4(cat.)氧化

Abstract: A concise synthesis procedure for the total synthesis of natural product(±)-Aiphanol 12, a novel stilbenolignan having a stilbene-phenylpropane unit with a dioxane moiety, was achieved by using simple aldehydes as the starting materials. The key steps were oxidative coupling of coniferyl alcohol 4 with catechol 6 using Ag2O as the catalyst to give the 1,4-benzodioxane intermediate 7, followed by a selective protection of the phenolic hydroxy group of 7 to afford 8, which was oxidized by NaIO4/OsO4(cat.) to give the key intermediate aldehyde 9. Then after Wittig-Horner reaction followed by conversion of Z-isomer to E-isomer using thiophenol in refluxing benzene in the presence of azoisobutyronitrile(AIBN) to produce 11, which underwent deprotection with diluted HCl in methanol to afford the titled compound(±)-Aiphanol 12 conveniently.

Key words: ?(±)-Aiphanol, Stilbene, 1,4-Benzodioxane, Ag2O coupling reaction, NaIO4/OsO4(cat.) oxidation

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