有机化学 ›› 2018, Vol. 38 ›› Issue (1): 156-161.DOI: 10.6023/cjoc201708060 上一篇    下一篇

所属专题: 庆祝吴养洁院士九十华诞专辑

研究论文

Cudratricusxanthone B的全合成

周鹏飞, 侯爱君, 王洋   

  1. 复旦大学药学院 上海 201203
  • 收稿日期:2017-08-30 修回日期:2017-09-21 发布日期:2017-10-24
  • 通讯作者: 侯爱君, 王洋 E-mail:ajhou@shmu.edu.cn;wangyang@shmu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21472025,21172044,81222045,21372049)资助项目.

Total Synthesis of Cudratricusxanthone B

Zhou Pengfei, Hou Aijun, Wang Yang   

  1. School of Pharmacy, Fudan University, Shanghai 201203
  • Received:2017-08-30 Revised:2017-09-21 Published:2017-10-24
  • Contact: 10.6023/cjoc201708060 E-mail:ajhou@shmu.edu.cn;wangyang@shmu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21472025, 21172044, 81222045, 21372049).

以价廉易得的2,4-二羟基苯甲酸为起始原料,通过Claisen重排和选择性脱甲基等8步反应,以3.1%的总收率首次完成了具有生物活性的异戊烯基氧杂蒽酮类天然产物cudratricusxanthone B(1)的全合成,为该化合物进一步的生物活性研究奠定了物质基础.同时还合成得到另一氧杂蒽酮化合物2,证实文献报道的氧杂蒽酮类天然产物staudtiixanthone D结构鉴定有误.

关键词: Cudratricusxanthone B, 异戊烯基氧杂蒽酮, Claisen重排, 全合成

The efficient total synthesis of cudratricusxanthone B (1), a biologically interesting natural isoprenylated xanthone, has been achieved for the first time starting from commercially available 2,4-dihydroxybenzoic acid via a linear reaction sequence of 8 steps with the overall yield of 3.1%, wherein Claisen rearrangement and demethylation with AlCl3/pyridine are used as key reactions. This work definitely laid the foundation for the further pharmacological study of this natural compound. Meanwhile, another xanthone (2) has been synthesized, which proved the reported structure of the natural xanthone staudtiixanthone D to be wrong.

Key words: cudratricusxanthone B, isoprenylated xanthone, Claisen rearrangement, total synthesis