高等学校化学学报

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Ligudentatin A的全合成

张晨曦, 毕福强, 李裕林   

  1. 兰州大学有机化学研究所, 功能有机分子化学国家重点实验室, 兰州 730000
  • 收稿日期:2008-04-01 修回日期:1900-01-01 出版日期:2008-11-10 发布日期:2008-11-10
  • 通讯作者: 李裕林

Total Synthesis of Ligudentatin A

ZHANG Chen-Xi, BI Fu-Qiang, LI Yu-Lin*   

  1. State Key Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2008-04-01 Revised:1900-01-01 Online:2008-11-10 Published:2008-11-10
  • Contact: LI Yu-Lin

摘要: 以(+)-紫苏醇2为起始原料, 经氧化、Witting、Diels-Alder和烯酮的芳构化等反应, 最终以17.7%的总收率完成了去甲基倍半萜Ligudentatin A(1)的全合成, 其中Diels-Alder和烯酮的芳构化反应为关键步骤.

关键词: Ligudentatin A, 全合成, Diels-Alder反应, 芳构化反应

Abstract: Ligudentatin A(1), a new phenolic norsesquiterpenes, was first synthesized starting from (+)-perillalalcohol 2 through six steps, successively, with an overall yield of 17.7%. The key steps were the Diels-Alder reaction and aromatization of enone to phenol. The advantages of this approach are reasonable yields and the ease with which the reaction can be carried out with readily available materials and reagents under mild conditions.

Key words: Ligudentatin A, Total synthesis, Diels-Alder reaction, Aromatization

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