2. Academic Validation
  3. 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

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

  • J Org Chem. 2017 Apr 21;82(8):4148-4159. doi: 10.1021/acs.joc.7b00044.
Qiao Yan 1,  Emma Gin 1,  Malgorzata Wasinska-Kalwa 1,  Martin G Banwell 1,  Paul D Carr 1
Affiliations

Affiliation

  • 1 Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, Australian Capital Territory 2601, Australia.
PMID: 28225623 DOI: 10.1021/acs.joc.7b00044
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.

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