A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin
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- 作者：Alois Plodek ; Stephan Raeder ; Franz Bracher
- 关键词：Alkaloids ; Pyridoacridines ; Homolytic acylation ; Friedel&ndash ; Crafts acylation ; Cyclization ; Trifluoromethanesulfonic acid
- 刊名：Tetrahedron
- 出版年：2013
- 出版时间：18 November, 2013
- 年：2013
- 卷：69
- 期：46
- 页码：9857-9864
- 全文大小：619 K
文摘
A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin starting from readily available 4-bromobenzo[c][2,7]naphthyridine (<strong class=""boldFont"">10strong>) comprises a high-yield Minisci-type homolytic methoxycarbonylation at C-5, followed by introduction of the ring A scaffold via Suzuki cross-coupling reaction, and a trifluoromethanesulfonic acid-aided Friedel-Crafts-type intramolecular acylation. This protocol allows for the introduction of various electron-rich carbocyclic and heterocyclic ring A substitutes.