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Communication | Regular issue | Vol 65, No. 7, 2005, pp.1561-1567
Published online, 28th April, 2005
DOI: 10.3987/COM-05-10418
Total Synthesis of Murrastifoline-A by Way of the Pd-catalyzed Double N-Arylation of a Carbazolamine with a 2,2’-Dibromobiphenyl Derivative

Takafumi Kitawaki, Yoko Hayashi, and Noritaka Chida*

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan

Abstract

The first total synthesis of murrastifoline-A (1), a biscarbazole alkaloid is described. The biscarbazole skeleton of 1 was effectively constructed by the Pd-catalyzed double N-arylation of carbazolamine (bottom-half segment, 3) with dibromobiphenyl derivative (top-half segment, 2) in one-step reaction. Both segments were synthesized starting from 2-amino-5-methylphenol (4).