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

✍ Scribed by Pablo Bernal; Joaquín Tamariz

Publisher: John Wiley and Sons
Year: 2007
Tongue: German
Weight: 80 KB
Volume: 90
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200790148

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✦ Synopsis

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 synthesis, in which such a diarylamine derivative was transformed into 1 by a Pd^II^‐stoichiometric cyclization, this new approach comprised an improved cyclization through a more efficient Pd^0^‐catalyzed intramolecular diaryl coupling which was applied to 9, thus obtaining the natural carbazole 1 in a higher overall yield.

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