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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 12: 2515 - 2519

DOI: https://doi.org/10.6023/cjoc201308005

Articles

Formal Synthesis of (－)-Frontalin

  • Zhou Hang ,
  • Sun Moran ,
  • Cao Qiwei ,
  • Zhu Ming ,
  • Bai Leiyang ,
  • Xie Yangla ,
  • Yang Hua
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  • a School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001;
    b Haikou Center for Disease Control and Prevention, Haikou 571000

Received date: 2013-08-05

  Revised date: 2013-09-21

  Online 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).

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Abstract

(－)-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

Cite this article

Zhou Hang , Sun Moran , Cao Qiwei , Zhu Ming , Bai Leiyang , Xie Yangla , Yang Hua . Formal Synthesis of (－)-Frontalin[J]. Chinese Journal of Organic Chemistry, 2013 , 33(12) : 2515 -2519 . DOI: 10.6023/cjoc201308005

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