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Synthesis of a Regular 24-membered Cyclodepsipeptide by Direct Amide Cyclization


Köttgen, P; Linden, Anthony; Heimgartner, Heinz (2009). Synthesis of a Regular 24-membered Cyclodepsipeptide by Direct Amide Cyclization. Zeitschrift fuer Naturforschung. Section B: A Journal of Chemical Sciences, 64b(4):689-698.

Abstract

The synthesis of a 24-membered cyclic depsipeptide with an alternating sequence of phenyllactic acid and α-aminoisobutyric acid (Aib) is described. The linear precursor was prepared via the ‘azirine/oxazolone method’ using 2,2-dimethyl-3-amino-2H-azirines as building blocks for the α,α-disubstituted α-amino acid Aib. The macrolactonization leading to the cyclodepsipeptide was achieved by the ‘direct amide cyclization’, i. e., by treatment of a solution of the linear precursor in toluene with HCl gas.

Abstract

The synthesis of a 24-membered cyclic depsipeptide with an alternating sequence of phenyllactic acid and α-aminoisobutyric acid (Aib) is described. The linear precursor was prepared via the ‘azirine/oxazolone method’ using 2,2-dimethyl-3-amino-2H-azirines as building blocks for the α,α-disubstituted α-amino acid Aib. The macrolactonization leading to the cyclodepsipeptide was achieved by the ‘direct amide cyclization’, i. e., by treatment of a solution of the linear precursor in toluene with HCl gas.

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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
Scopus Subject Areas:Physical Sciences > General Chemistry
Uncontrolled Keywords:Cyclodepsipeptides, Direct Amide Cyclization, Azirine/Oxazolone Method, Aminoisobutyric Acid, Crystal Structure
Language:English
Date:2009
Deposited On:25 Nov 2009 08:09
Last Modified:23 Jan 2022 14:58
Publisher:Verlag der Zeitschrift für Naturforschung
ISSN:0932-0776
Funders:University of Zurich, F. Hoffmann-La Roche AG, Basel
Additional Information:Free access at Official URL
OA Status:Green
Official URL:http://www.znaturforsch.com/rb/s64b0689.pdf

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