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Synthesis 2012(2): 290-296  
DOI: 10.1055/s-0031-1289652
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

First Synthesis of Benzopyridoiodolium Salts and Twofold Buchwald-Hartwig Amination for the Total Synthesis of Quindoline

Julien Letessier, Heiner Detert*
Institute for Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Fax: +49(6131)3925338; e-Mail: detert@uni-mainz.de;
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Publication History

Received 12 August 2011
Publication Date:
22 December 2011 (online)

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Abstract

The first synthesis of cyclic benzopyridoiodolium salts is described. These hypervalent iodine intermediates are used in an efficient strategy for the construction of the δ-carboline core. This novel approach involves a twofold palladium-catalyzed Buchwald-Hartwig reaction between these unprecedented reagents and a primary amine. Our methodology successfully provides the expected N-substituted δ-carboline core and is efficiently applied in the total synthesis of quindoline.

Key words

alkaloids - amination - heterocycles - iodine - total synthesis

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