Total synthesis of (±)-chartelline C
Total synthesis of (±)-chartelline C
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DOI：
10.1021/ja0659673
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发表时间：
2006-11-01
影响因子：
15
通讯作者：
Shenvi, Ryan A.
中科院分区：
文献类型：
--
作者：
Baran, Phil S.;Shenvi, Ryan A.
报道了首次以简明的10步反应全合成(±)-查特林C。完成这一长达数十年的谜题的亮点包括(1)化学和位置选择性地安装杂芳烃卤素，(2)无卤素的炔键的单还原，(3)灵敏的β-氯烯酰胺的简单放置策略，(4)乙烯基羧酸的异常容易的热分解，以及(5)在杂环化学中潜在的应用值得进一步研究的强大的环收缩。
The first total synthesis of (±)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive β-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation.