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

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)10459-10468
Number of pages10
JournalJournal of Organic Chemistry
Volume78
Issue number20
DOIs
Publication statusPublished - 2013 Oct 18

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Pyrroles
Skeleton
Metabolites
Proline
Nitrogen
ugibohlin
prolinamide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and unexpected oxidization of the tricyclic core of ugibohlin, isophakellin, and styloguanidine. / Chang, Chia Wei; Wu, Chi Cheng; Chang, Yung Yu; Lin, Chia Chi; Chien, Tun-Cheng.

In: Journal of Organic Chemistry, Vol. 78, No. 20, 18.10.2013, p. 10459-10468.

Research output: Contribution to journalArticle

Chang, Chia Wei ; Wu, Chi Cheng ; Chang, Yung Yu ; Lin, Chia Chi ; Chien, Tun-Cheng. / Synthesis and unexpected oxidization of the tricyclic core of ugibohlin, isophakellin, and styloguanidine. In: Journal of Organic Chemistry. 2013 ; Vol. 78, No. 20. pp. 10459-10468.
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