Construction of functionalized B/C/D ring system of C19-diterpenoid alkaloids via intramolecular Diels-Alder reaction followed by Wagner-Meerwein rearrangement
Construction of functionalized B/C/D ring system of C19-diterpenoid alkaloids via intramolecular Diels-Alder reaction followed by Wagner-Meerwein rearrangement
复制标题
DOI：
10.1016/j.tet.2011.11.063
复制
发表时间：
2012-01-28
期刊：
影响因子：
2.1
通讯作者：
Wang, Feng-Peng
中科院分区：
文献类型：
--
作者：
Cheng, Hang;Xu, Liang;Wang, Feng-Peng
描述了构建 C-19-二萜生物碱 B/C/D 环系统的简明策略，其特点是掩蔽邻苯醌的高度非对映选择性分子内 Diels-Alder 反应和有效的 Wagner-Meerwein 1,2-shift 重排。重排产物19的官能团转化证明了在许多类型的C-19-二萜生物碱的D环上立体选择性安装氧官能团的潜力。 (C) 2011 Elsevier Ltd. 保留所有权利。
A concise strategy for construction of B/C/D ring system of C-19-diterpenoid alkaloids was described, which features a highly diastereoselective intramolecular Diels-Alder reaction of masked o-benzoquinone and an efficient Wagner-Meerwein 1,2-shift rearrangement. The functional group transformations of rearrangement product 19 demonstrate a potential for stereoselective installation of oxygen functions on D-ring of many type of C-19-diterpenoid alkaloids. (C) 2011 Elsevier Ltd. All rights reserved.