化学学报 ›› 2005, Vol. 63 ›› Issue (20): 1901-1905. 上一篇    下一篇

研究论文

(±) Cudraflavanone B及(±)-5-O-Methyl Cudraflavanone B的全合成研究

杨永刚,张宇,曹小平*   

  1. (兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000)
  • 收稿日期:2005-04-06 修回日期:2005-06-28 出版日期:2005-10-28 发布日期:2010-12-10
  • 通讯作者: 曹小平

The First Total Synthesis of (±) Cudraflavanone B and (±)-5-O-Methyl Cudraflavanone B

YANG Yong-Gang, ZHANG Yu, CAO Xiao-Ping*   

  1. (State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou 730000)
  • Received:2005-04-06 Revised:2005-06-28 Online:2005-10-28 Published:2010-12-10
  • Contact: CAO Xiao-Ping

以2,4,6-三羟基苯乙酮和2,4-二羟基苯甲醛为起始原料, 经过异戊烯基取代、选择性保护羟基、Mitsunobu反应、Claisen重排、醛酮缩合、催化环化及去保护基等步骤, 首次完成了天然异戊烯基黄烷酮Cudraflavanone B的全合成, 同时也完成了(±)-5-O-甲基-6-(2"-异戊烯基)-7,2',4'-三羟基黄烷酮的全合成研究.

关键词: 选择性保护, Claisen重排, 醛酮缩合, 催化关环

The total synthesis of natural Cudraflavanone B was first achieved through selective protection of phenolic hydroxyl groups, Mitsunobu reaction, Claisen rearrangement, condensation, cyclization and deprotection starting from 2,4,6-trihydroxyacetophenone and 2,4-dihydroxybenzaldehyde. Meanwhile, the total synthesis of (±)-5-O-methyl-6-(2"-prenyl)-7,2',4'-trihydroxyflavanone was also finished.

Key words: selective protection, Claisen rearrangement, condensation, cyclization