Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (12): 2515-2519.DOI: 10.6023/cjoc201308005 Previous Articles     Next Articles



周航a, 孙默然a, 曹其伟a, 朱明b, 白磊阳a, 谢阳腊a, 杨华a   

  1. a 郑州大学药学院 郑州 450001;
    b 海口市疾病预防控制中心 海口 571000
  • 收稿日期:2013-08-05 修回日期:2013-09-21 发布日期:2013-09-25
  • 通讯作者: 杨华
  • 基金资助:

    国家自然科学基金(No. 21372205)及郑州大学研究生科学研究(No. 12Y03303)资助项目.

Formal Synthesis of (-)-Frontalin

Zhou Hanga, Sun Morana, Cao Qiweia, Zhu Mingb, Bai Leiyanga, Xie Yanglaa, Yang Huaa   

  1. a School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001;
    b Haikou Center for Disease Control and Prevention, Haikou 571000
  • Received:2013-08-05 Revised:2013-09-21 Published:2013-09-25
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21372205) and the Graduate Research Project of Zhengzhou University (No. 2Y03303).

(-)-Frontalin is usually used as one of standard molecules to test the usefulness of chiral tertiary alcohol construction. Based on methodology of chiral tertiary alcohols construction via [2,3]-Meisenheimer rearrangement which has been developing on our laboratory, the formal synthesis of (-)-frontalin is finished via successive Wittig reaction, ester reduction, [2,3]-Meisenheimer rearrangement, and etc. The total yield is 34% and the ee value is 94%. The substrate scope is expanded from α,β-conjugated olefins into isolated olefins. This proves the more general characteristic of chiral tertiary alcohol construction via [2,3]-Meisenheimer rearrangement.

Key words: (-)-frontalin, chiral tertiary alcohol, [2,3]-Meisenheimer rearrangement, Wittig reaction