Actinobenzoquinoline and Actinophenanthrolines A-C, Unprecedented Alkaloids from a Marine Actinobacterium

Sang Jip Nam; Christopher A. Kauffman; Paul R. Jensen; Curtis E. Moore; Arnold L. Rheingold; William Fenical

doi:10.1021/acs.orglett.5b01387

Actinobenzoquinoline and Actinophenanthrolines A-C, Unprecedented Alkaloids from a Marine Actinobacterium

Sang Jip Nam, Christopher A. Kauffman, Paul R. Jensen, Curtis E. Moore, Arnold L. Rheingold, William Fenical

Department of Chemistry & Nanoscience

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

24 Scopus citations

Abstract

(Chemical Equation Presented) Chemical investigation of a marine actinomycete within the family Streptomycetaceae (our strain CNQ-149) has led to the isolation of the unprecedented alkaloids, actinobenzoquinoline (1) and actinophenanthrolines A-C (2-4). The chemical structures of 1-4 were assigned by interpretation of NMR spectroscopic data, and their absolute configurations were assigned by X-ray analysis. Actinobenzoquinoline possesses a 5-methyloxazolidin-4-one moiety and a dihydrobenzo[h]quinoline core structure, while actinophenanthrolines A-C are composed of hydroxypropanamide-substituted 1,7-phenanthroline core skeletons.

Original language	English
Pages (from-to)	3240-3243
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.5b01387
State	Published - 2 Jul 2015

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© 2015 American Chemical Society.

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title = "Actinobenzoquinoline and Actinophenanthrolines A-C, Unprecedented Alkaloids from a Marine Actinobacterium",

abstract = "(Chemical Equation Presented) Chemical investigation of a marine actinomycete within the family Streptomycetaceae (our strain CNQ-149) has led to the isolation of the unprecedented alkaloids, actinobenzoquinoline (1) and actinophenanthrolines A-C (2-4). The chemical structures of 1-4 were assigned by interpretation of NMR spectroscopic data, and their absolute configurations were assigned by X-ray analysis. Actinobenzoquinoline possesses a 5-methyloxazolidin-4-one moiety and a dihydrobenzo[h]quinoline core structure, while actinophenanthrolines A-C are composed of hydroxypropanamide-substituted 1,7-phenanthroline core skeletons.",

author = "Nam, \{Sang Jip\} and Kauffman, \{Christopher A.\} and Jensen, \{Paul R.\} and Moore, \{Curtis E.\} and Rheingold, \{Arnold L.\} and William Fenical",

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doi = "10.1021/acs.orglett.5b01387",

language = "English",

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T1 - Actinobenzoquinoline and Actinophenanthrolines A-C, Unprecedented Alkaloids from a Marine Actinobacterium

AU - Nam, Sang Jip

AU - Kauffman, Christopher A.

AU - Jensen, Paul R.

AU - Moore, Curtis E.

AU - Rheingold, Arnold L.

AU - Fenical, William

PY - 2015/7/2

Y1 - 2015/7/2

N2 - (Chemical Equation Presented) Chemical investigation of a marine actinomycete within the family Streptomycetaceae (our strain CNQ-149) has led to the isolation of the unprecedented alkaloids, actinobenzoquinoline (1) and actinophenanthrolines A-C (2-4). The chemical structures of 1-4 were assigned by interpretation of NMR spectroscopic data, and their absolute configurations were assigned by X-ray analysis. Actinobenzoquinoline possesses a 5-methyloxazolidin-4-one moiety and a dihydrobenzo[h]quinoline core structure, while actinophenanthrolines A-C are composed of hydroxypropanamide-substituted 1,7-phenanthroline core skeletons.

AB - (Chemical Equation Presented) Chemical investigation of a marine actinomycete within the family Streptomycetaceae (our strain CNQ-149) has led to the isolation of the unprecedented alkaloids, actinobenzoquinoline (1) and actinophenanthrolines A-C (2-4). The chemical structures of 1-4 were assigned by interpretation of NMR spectroscopic data, and their absolute configurations were assigned by X-ray analysis. Actinobenzoquinoline possesses a 5-methyloxazolidin-4-one moiety and a dihydrobenzo[h]quinoline core structure, while actinophenanthrolines A-C are composed of hydroxypropanamide-substituted 1,7-phenanthroline core skeletons.

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DO - 10.1021/acs.orglett.5b01387

M3 - Article

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

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ER -

Actinobenzoquinoline and Actinophenanthrolines A-C, Unprecedented Alkaloids from a Marine Actinobacterium

Abstract

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