Synthesis and unexpected oxidization of the tricyclic core of ugibohlin, isophakellin, and styloguanidine

Chia Wei Chang, Chi Cheng Wu, Yung Yu Chang, Chia Chi Lin, Tun Cheng Chien*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

7 引文 斯高帕斯(Scopus)

摘要

A series of 4-substituted 5,6,7,9-tetrahydropyrrolo[2,3-f]indolizin-9-ones, representing the tricyclic core skeleton of ugibohlin, isophakellin, and styloguanidine, were synthesized via an intramolecular Vilsmeier-Haack reaction. This reaction allows the chemoselective C-C bond formation between the pyrrole C3 and proline C5 of N-[(pyrrol-2-yl)carbonyl]prolinamides to construct the B-ring without the protection of the pyrrole nitrogen. Unexpected oxidizative property of the tricyclic core skeleton was observed, which could illuminate understanding of the biological formation of these marine secondary metabolites.

原文英語
頁(從 - 到)10459-10468
頁數10
期刊Journal of Organic Chemistry
78
發行號20
DOIs
出版狀態已發佈 - 2013 10月 18

ASJC Scopus subject areas

  • 有機化學

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