Formal Synthesis of (－)-Frontalin

doi:10.6023/cjoc201308005

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

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(－)-Frontalin的形式合成

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

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 E-mail:yanghua@zzu.edu.cn
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 Hang^a, Sun Moran^a, Cao Qiwei^a, Zhu Ming^b, Bai Leiyang^a, Xie Yangla^a, Yang Hua^a

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

Cite this article

Zhou Hang, Sun Moran, Cao Qiwei, Zhu Ming, Bai Leiyang, Xie Yangla, Yang Hua. Formal Synthesis of (－)-Frontalin[J]. Chin. J. Org. Chem., 2013, 33(12): 2515-2519.

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(－)-Frontalin的形式合成

Formal Synthesis of (－)-Frontalin

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