Verbenachalcone的另法全合成

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (7): 1342.

Verbenachalcone的另法全合成

张应鹏, 陈宇涛, 杨云裳, 关晓

兰州理工大学石油化工学院, 有机与药物化学研究所, 兰州 730050

收稿日期:2009-11-30 出版日期:2010-07-10 发布日期:2010-07-10
通讯作者: 张应鹏, 男, 博士, 副教授, 主要从事生物有机化学研究. E-mail: yingpengzhang@126.com
基金资助:
甘肃省自然科学基金(批准号: 3ZS062-B25-017)资助.

Modified Total Synthesis of Verbenachalcone

ZHANG Ying-Peng*, CHEN Yu-Tao, YANG Yun-Shang, GUAN Xiao

Institute of Organic & Pharmaceutical Chemistry, School of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou 730050, China

Received:2009-11-30 Online:2010-07-10 Published:2010-07-10
Contact: ZHANG Ying-Peng. E-mail: yingpengzhang@126.com
Supported by:
甘肃省自然科学基金(批准号: 3ZS062-B25-017)资助.

摘要/Abstract

摘要：

用一种新的简便方法对Verbenachalcone进行全合成, 针对目标物的结构特征, 将其切为2个合成片段, 即化合物4和6, 然后再将2个片段连接. 从对羟基苯甲醛(2)开始经过溴代、乙酰化、Ullmann反应、甲氧甲基化、羟醛缩合、脱保护和催化加氢等7步反应完成了标题化合物的全合成, 总收率为39.1%, 合成的关键步骤是3-溴-4-羟基苯甲醛(3)和香兰素进行的Ullmann反应. 关键中间体与最终产物的化学结构经¹H NMR, ¹³C NMR和ESI-MS等表征确认.

关键词: Verbenachalcone; Ullmann反应; 全合成; 羟醛缩合

Abstract:

A new and simple method for synthesis of verbenachalcone(1) was reported. A method for reverse synthesis design was adopted to two synthetic fragments, compound 4 and compound 6. Then the two fragments were combined together, starting from p-hydroxybenzaldehyde(2) through acetylation, bromination, Ullmann reaction, methoxymethylation, aldol condensation, deprotection, catalytic hydrogenation seven steps to target compound, with total yield of 39.1%. The key steps were the Ullmann reaction of 3-bromo-4-hydroxybenzaldehyde(3) with vanilline. The chemical structures of the key intermediate and final target product were verified by ¹H NMR, ¹³C NMR and ESI-MS.

Key words: Verbenachalcone; Ullmann reaction; Total synthesis; Aldol condensation

TrendMD:

张应鹏, 陈宇涛, 杨云裳, 关晓. Verbenachalcone的另法全合成. 高等学校化学学报, 2010, 31(7): 1342.

ZHANG Ying-Peng*, CHEN Yu-Tao, YANG Yun-Shang, GUAN Xiao. Modified Total Synthesis of Verbenachalcone. Chem. J. Chinese Universities, 2010, 31(7): 1342.

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