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Synthesis of Enniatin-like Cyclic Depsipeptides via direct Amide Cyclization


Köttgen, P; Linden, A; Heimgartner, H (2006). Synthesis of Enniatin-like Cyclic Depsipeptides via direct Amide Cyclization. Helvetica Chimica Acta, 89(4):731-746.

Abstract

The synthesis of several 18-membered cyclodepsipeptides with an alternating sequence of a,a-disubstituted a-amino acids and a-hydroxy acids (compounds 14a–14e) is described. The ring closure via macrolactonization
was accomplished by treatment of a diluted suspension of the corresponding linear precursors 12a–12e in toluene with HCl gas, i.e., the so-called 'direct amide cyclization'. The incorporation of the a,a-disubstituted a-amino acids was achieved via the 'azirine/oxazolone method' with 2H-azirin-3-amines of type 6 and 9 as building blocks. The structure of the cyclic depsipeptide 14a was established by X-ray crystallography.

Abstract

The synthesis of several 18-membered cyclodepsipeptides with an alternating sequence of a,a-disubstituted a-amino acids and a-hydroxy acids (compounds 14a–14e) is described. The ring closure via macrolactonization
was accomplished by treatment of a diluted suspension of the corresponding linear precursors 12a–12e in toluene with HCl gas, i.e., the so-called 'direct amide cyclization'. The incorporation of the a,a-disubstituted a-amino acids was achieved via the 'azirine/oxazolone method' with 2H-azirin-3-amines of type 6 and 9 as building blocks. The structure of the cyclic depsipeptide 14a was established by X-ray crystallography.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2006
Deposited On:22 May 2012 06:48
Last Modified:21 Nov 2017 15:42
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Swiss National Science Foundation , Betty Sassella-Keller Legat, f. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200690069

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