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Synlett 2010(11): 1685-1687  
DOI: 10.1055/s-0029-1219961
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Botryllamides and Lansiumamides via Ruthenium-Catalyzed Hydroamidation of Alkynes

Lukas J. Gooßen*, Mathieu Blanchot, Matthias Arndt, Kifah S. M. Salih
Institut für Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str., Building 54, 67663 Kaiserslautern, Germany
Fax: +49(631)2053921; e-Mail: goossen@chemie.uni-kl.de;
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Publication History

Received 26 March 2010
Publication Date:
04 June 2010 (online)

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Abstract

Ruthenium-catalyzed hydroamidations of alkynes allow a concise synthetic entry to both E- and Z-configured enamide natural products. This was demonstrated by the synthesis of botryllamides C and E, lansiumamides A and B, and lansamide I in 1-3 steps and 57-98% yield from simple, commercially available precursors.

Key words

alkyne - botryllamide - hydroamidation - lansamide - lansiumamide - ruthenium

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13

CCDC 768748 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

14

CCDC 768747 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.