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Synthesis of conformationally restricted cyclic hexadepsipeptides via direct amide cyclization


Koch, Kristian N; Heimgartner, Heinz (2000). Synthesis of conformationally restricted cyclic hexadepsipeptides via direct amide cyclization. Helvetica Chimica Acta, 83:1881-1900.

Abstract

Ring closure by direct amide cyclization was used in the synthesis of 19-membered cyclic depsipeptides 27 (Schemes1 and 3). The linear hexapeptide precursors 4, containing the beta-hydroxy acid 3-hydroxy-2-phenylpropanoic acid (Tro), and five alpha-amino acids of the type Aib, Gly, and Pro, were prepared according to Scheme 2. The alpha,alpha-disubstituted alpha-amino acid Aib was incorporated into the peptide chain via the azirine/oxazolone method, and Gly and Pro were introduced by using the TBTU/HOBt coupling method. The cyclic depsipeptides 27a - 27f were obtained in reasonable-to-excellent yields (Scheme 3 and Table 1).

Abstract

Ring closure by direct amide cyclization was used in the synthesis of 19-membered cyclic depsipeptides 27 (Schemes1 and 3). The linear hexapeptide precursors 4, containing the beta-hydroxy acid 3-hydroxy-2-phenylpropanoic acid (Tro), and five alpha-amino acids of the type Aib, Gly, and Pro, were prepared according to Scheme 2. The alpha,alpha-disubstituted alpha-amino acid Aib was incorporated into the peptide chain via the azirine/oxazolone method, and Gly and Pro were introduced by using the TBTU/HOBt coupling method. The cyclic depsipeptides 27a - 27f were obtained in reasonable-to-excellent yields (Scheme 3 and Table 1).

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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:2000
Deposited On:29 Oct 2013 10:48
Last Modified:07 Dec 2017 23:12
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/1522-2675(20000809)83:8<1881::AID-HLCA1881>3.0.CO;2-G

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