Helvetica Chimica Acta

Total Synthesis of Murrayanine Involving 4, 5??Dimethyleneoxazolidin??2??ones and a Palladium (0)??Catalyzed Diaryl Insertion

P Bernal, J Tamariz

Index: Bernal, Pablo; Tamariz, Joaquin Helvetica Chimica Acta, 2007 , vol. 90, # 8 p. 1449 - 1454

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Citation Number: 13

Abstract

Abstract A new total synthesis of the natural carbazole murrayanine (1) was developed by using the 4, 5-dimethyleneoxazolidin-2-one 12 as starting material. The latter underwent a highly regioselective Diels–Alder cycloaddition with acrylaldehyde (= prop-2-enal; 13) to give adduct 14 (Scheme 3). Conversion of this adduct into diarylamine derivative 9 was carried out via hydrolysis and methylation (Scheme 4). Differing from our previous ...