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Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-62076

Iliev, Boyan; Linden, Anthony; Kunz, Roland; Heimgartner, Heinz (2006). 14-Membered cyclodepsipeptides with alternating beta-hydroxy and alpha-amino acids by cyclodimerization. Tetrahedron, 62(6):1079-1094.

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Abstract

The cyclodimerization (twinning) of beta-hydroxy acid amides of type 1 under ‘direct amide cyclization’ (DAC) conditions is described. Although other coupling methods also gave moderate results, best yields were obtained via DAC, reaching 88% for the cyclodimer 10. In all cases, when starting with racemic material, only the trans-substituted cyclodepsipeptides were isolated. Simple molecular modeling revealed that the formation of the cyclodimer is thermodynamically slightly more favorable than that of the cyclomonomer. The proposal that cyclodimer formation is preferred because of the presence of intramolecular H-bonds could not be confirmed by X-ray crystallography. The influence of substituents, both in the amino acid and in the hydroxy acid moieties, was also studied. It is shown, that cyclodimerization was successful only when the hydroxy acid moiety is alpha,alpha-disubstituted.

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Institute of Organic Chemistry
DDC:540 Chemistry
Language:English
Date:2006
Deposited On:22 May 2012 09:26
Last Modified:18 Apr 2014 21:49
Publisher:Elsevier
ISSN:0040-4020
Funders:Swiss National Science Foundation , F. Hoffmann-La Roche AG, Basel
Publisher DOI:10.1016/j.tet.2005.11.002
Citations:Web of Science®. Times Cited: 19
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