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

doi:10.1021/jo401911a

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	10459-10468
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	78
Issue number	20
DOIs	https://doi.org/10.1021/jo401911a
Publication status	Published - 2013 Oct 18

ASJC Scopus subject areas

Organic Chemistry

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

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.",

author = "Chang, {Chia Wei} and Wu, {Chi Cheng} and Chang, {Yung Yu} and Lin, {Chia Chi} and Tun-Cheng Chien",

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doi = "10.1021/jo401911a",

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journal = "Journal of Organic Chemistry",

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T1 - Synthesis and unexpected oxidization of the tricyclic core of ugibohlin, isophakellin, and styloguanidine

AU - Chang, Chia Wei

AU - Wu, Chi Cheng

AU - Chang, Yung Yu

AU - Lin, Chia Chi

AU - Chien, Tun-Cheng

PY - 2013/10/18

Y1 - 2013/10/18

N2 - 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.

AB - 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.

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

Abstract

ASJC Scopus subject areas

UN SDGs

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