期刊
ORGANIC CHEMISTRY FRONTIERS
卷 4, 期 12, 页码 2417-2421出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7qo00678k
关键词
-
资金
- National Natural Science Foundation of China [31470416, 81430092]
- Outstanding Youth Fund of the Basic Research Program of Jiangsu Province [BK20160077]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT_15R63]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
Tooniliatone A (1), a novel limonoid with an unprecedented 6/5/6/5 tetracarbocyclic skeleton was isolated from Toona ciliata Roem. var. yunnanensis. Its rearranged ring-seco backbone was proposed to biosynthetically originate from co-isolated known toonacilin (3) via a rare electron-deficient alkene electrophilic cyclization and 1,2-alkyl shift sequence. The acid-catalyzed biomimetic conversion of 3 not only successfully afforded 1 but also another novel 6/5/6/5 tetracarbocyclic skeleton, tooniliatone B (2). The priority of 2 in this biomimetic conversion, the existence of 1 and the absence of 2 in the crude extract suggested the biosynthetic selectivity of 1 from 3. The divergent biomimetic sequence, based on a carbocation from an epoxide moiety, provided an inspiration for constructing complex polycyclic carbon skeletons.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据