Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (09): 1939-1944.DOI: 10.6023/cjoc201307011 Previous Articles     Next Articles



高凯歌a, 孙默然a, 朱明b, 周航a, 曹其伟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:2013-07-06 修回日期:2013-07-27 发布日期:2013-08-13
  • 通讯作者: 杨华
  • 基金资助:

    国家自然科学基金(No. 21372205)资助项目

Synthesis of Right Segment of Ingramycin

Gao Kaigea, Sun Morana, Zhu Mingb, Zhou Hanga, Cao Qiweia, Yang Huaa   

  1. a School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001;
    b Haikou Center for Diease Control and Prevention, Haikou 571000
  • Received:2013-07-06 Revised:2013-07-27 Published:2013-08-13
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21372205)

The right segment of ingramycin contains a synthesis-challenging chiral tertiary alcohol structural motif. Based on methodology developed on our laboratory to construct chiral tertiary alcohols via[2,3]-Meisenheimer rearrangement, the synthesis of right segment of ingramycin was successfully achieved over fifteen steps via successive Wittig reaction,[2,3]-Meisenheimer rearrangement, selective ester group reduction with NaBH4, and etc. The total yield was 28% and ee value was 90%.

Key words: ingramycin, chiral tertiary alcohol, [2,3]-Meisenheimer rearrangement, Wittig reaction, selective ester reduction with NaBH4