Solid-phase synthesis of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones via a cyclization/release strategy

A solid-phase synthesis procedure for the parallel preparation of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones is described. The methodology applies α- and alicyclic β-amino acid building blocks to construct the seven-membered heterocyclic core, while alcohols are used for further skeletal decorat...

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Bibliographic Details
Published in:Tetrahedron 2016-01, Vol.72 (1), p.148-160
Main Authors: Caroen, Jurgen, Clemmen, An, Kámán, Judit, Backaert, Fréderique, Goeman, Jan L., Fülöp, Ferenc, Van der Eycken, Johan
Format: Article
Language:English
Subjects:
1,4-Diazepane-2,5-diones
Conformational analysis of cyclic dipeptides
Cyclization/release strategy
Homodiketopiperazines
Solid-phase synthesis
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Summary:A solid-phase synthesis procedure for the parallel preparation of 6,7-cycloalkane-fused 1,4-diazepane-2,5-diones is described. The methodology applies α- and alicyclic β-amino acid building blocks to construct the seven-membered heterocyclic core, while alcohols are used for further skeletal decoration. The use of a cyclization/release strategy permits the isolation of the target cyclic α,β-dipeptides in good crude purities and generally moderate to good yields. A 26-membered model library is reported and NMR spectroscopical data are used to describe the overall conformational behaviour of the obtained homodiketopiperazines. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.11.023