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
  • 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.

Products