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Synthesis 2009(15): 2605-2615  
DOI: 10.1055/s-0029-1217400
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed [1,3]-Dipolar Cycloaddition for the Synthesis of Macrocycles Containing Acyclic, Aromatic and Steroidal Moieties

Gennadij V. Latyshev, Mikhail S. Baranov, Alexei V. Kazantsev, Alexei D. Averin, Nikolay V. Lukashev*, Irina P. Beletskaya
Chemistry Department, Moscow State Lomonosov University, Vorobievy Gory, 1, str. 3, 119991 Moscow, Russian Federation
Fax: +7(495)4223297; e-Mail: nvluk@org.chem.msu.ru;
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Publikationsverlauf

Received 20 March 2009
Publikationsdatum:
22. Juni 2009 (online)

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Abstract

Copper-catalyzed 1,3-dipolar cycloaddition reactions are used for the synthesis of a series of bis(1,2,3-triazole)-containing macrocycles possessing acyclic, aromatic and steroidal fragments. The influence of the nature of the substituents on the diazides, and the length of the dialkyne-linking chain, in the substrates, on the product yields is studied. Macrocycles containing steroidal fragments are prepared via reactions of bis(cholane)-24,24′-diazides with aliphatic dipropargyl esters, or bis(cholane)-24,24′-dipropargyl esters with aromatic diazides, or by cyclization-dimerization of bile acid derivatives possessing both azide and acetylene groups in the same molecule.

Key words

1,3-dipolar cycloaddition - azides - cholaphanes - copper - macrocycles

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