高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (5): 955-959.doi: 10.7503/cjcu20190639

• 庆祝《高等学校化学学报》复刊40周年专栏 • 上一篇    下一篇

5,5,8aβ-三甲基-6β-羟基-反八氢-1-萘酮的合成及在Phenylspirodrimane类混源萜天然产物骨架构建中的应用

户志远1,万秋香1,周航1,宋传君1,*(),常俊标1,2,*()   

  1. 1. 郑州大学化学学院, 郑州 450001
    2. 河南师范大学化学化工学院, 新乡 453007
  • 收稿日期:2019-12-09 出版日期:2020-05-10 发布日期:2020-03-23
  • 通讯作者: 宋传君,常俊标 E-mail:chjsong@zzu.edu.cn;changjunbiao@zzu.edu.cn
  • 基金资助:
    国家自然科学基金委员会-河南联合基金(U1804283)

Synthesis of 6β-Hydroxy-5,5,8aβ-trimethyloctahydronaphthalen-1(2H)-one Toward the Establishment of the Scaffold of Phenylspirodrimane Meroterpenoid Natural Products

HU Zhiyuan1,WAN Qiuxiang1,ZHOU Hang1,SONG Chuanjun1,*(),CHANG Junbiao1,2,*()   

  1. 1. College of Chemistry, Zhengzhou University, Zhengzhou 450001, China
    2. School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
  • Received:2019-12-09 Online:2020-05-10 Published:2020-03-23
  • Contact: Chuanjun SONG,Junbiao CHANG E-mail:chjsong@zzu.edu.cn;changjunbiao@zzu.edu.cn
  • Supported by:
    † Supported by the National Natural Science Foundation of China-Henan United Fund(U1804283)

摘要:

以(E)-5,9-二甲基-4,8-癸二烯酸乙酯为原料, 发展了一种合成5,5,8aβ-三甲基-6β-羟基-反八氢-1-萘酮(1)的新方法, 并将其成功应用于phenylspirodrimane类混源萜天然产物骨架的构建. 对合成过程中所涉及的关键反应如区域选择性环氧化和Cp2TiCl催化的自由基串联环合反应进行了优化. 所合成化合物的结构均通过核磁共振波谱(NMR)和高分辨质谱(HRMS)进行了表征和确认.

关键词: 5,5,8aβ-三甲基-6β-羟基-反八氢-1-萘酮, Phenylspirodrimane类混源萜, 环氧化, 自由基串联环合反应

Abstract:

Starting from ethyl(E)-5,9-dimethyldeca-4,8-dienoate, we developed a method for the synthesis of 6β-hydroxy-5,5,8aβ-trimethyloctahydronaphthalen-1-one(1), which was successfully applied to the establishment of the skeleton of phenylspirodrimane meroterpenoid natural products. Key steps such as regioselective epoxidation and Cp2TiCl-promoted radical cascade cyclization have been optimized. The structures of the compounds synthesized have been characterized with nuclear magnetic resonance spectroscopy(NMR) and high resolution mass spectrometry(HRMS).

Key words: 6β-Hydroxy-5,5,8aβ-trimethyloctahydronaphthalen-1(2H)-one, Phenylspirodrimanes meroterpenoids, Epoxidation, Free radical tandem cyclization

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