A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A

Qiao Yan; Emma Gin; Malgorzata Wasinska-Kalwa; Martin G. Banwell; Paul D. Carr

doi:10.1021/acs.joc.7b00044

A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A

Qiao Yan, Emma Gin, Malgorzata Wasinska-Kalwa, Martin G. Banwell^*, Paul D. Carr

^*Corresponding author for this work

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

43 Citations (Scopus)

Abstract

The title natural products 2-7 have been prepared by reductive cyclization of the relevant 2-arylcyclohex-2-en-1-one (e.g. 20) to the corresponding tetrahydrocarbazole and dehydrogenation (aromatization) of this to give the target carbazole (e.g. 4). Compounds such as 20 were prepared using a palladium-catalyzed Ullmann cross-coupling reaction between the appropriate 2-iodocyclohex-2-en-1-one and o-halonitrobenzene.

Original language	English
Pages (from-to)	4148-4159
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	82
Issue number	8
DOIs	https://doi.org/10.1021/acs.joc.7b00044
Publication status	Published - 21 Apr 2017

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title = "A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A",

abstract = "The title natural products 2-7 have been prepared by reductive cyclization of the relevant 2-arylcyclohex-2-en-1-one (e.g. 20) to the corresponding tetrahydrocarbazole and dehydrogenation (aromatization) of this to give the target carbazole (e.g. 4). Compounds such as 20 were prepared using a palladium-catalyzed Ullmann cross-coupling reaction between the appropriate 2-iodocyclohex-2-en-1-one and o-halonitrobenzene.",

author = "Qiao Yan and Emma Gin and Malgorzata Wasinska-Kalwa and Banwell, {Martin G.} and Carr, {Paul D.}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

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doi = "10.1021/acs.joc.7b00044",

language = "English",

volume = "82",

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journal = "Journal of Organic Chemistry",

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A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A. / Yan, Qiao; Gin, Emma; Wasinska-Kalwa, Malgorzata et al.
In: Journal of Organic Chemistry, Vol. 82, No. 8, 21.04.2017, p. 4148-4159.

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

TY - JOUR

T1 - A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A

AU - Yan, Qiao

AU - Gin, Emma

AU - Wasinska-Kalwa, Malgorzata

AU - Banwell, Martin G.

AU - Carr, Paul D.

PY - 2017/4/21

Y1 - 2017/4/21

N2 - The title natural products 2-7 have been prepared by reductive cyclization of the relevant 2-arylcyclohex-2-en-1-one (e.g. 20) to the corresponding tetrahydrocarbazole and dehydrogenation (aromatization) of this to give the target carbazole (e.g. 4). Compounds such as 20 were prepared using a palladium-catalyzed Ullmann cross-coupling reaction between the appropriate 2-iodocyclohex-2-en-1-one and o-halonitrobenzene.

AB - The title natural products 2-7 have been prepared by reductive cyclization of the relevant 2-arylcyclohex-2-en-1-one (e.g. 20) to the corresponding tetrahydrocarbazole and dehydrogenation (aromatization) of this to give the target carbazole (e.g. 4). Compounds such as 20 were prepared using a palladium-catalyzed Ullmann cross-coupling reaction between the appropriate 2-iodocyclohex-2-en-1-one and o-halonitrobenzene.

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DO - 10.1021/acs.joc.7b00044

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A

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