A diastereoselective synthesis of the tetrahydropyridazinone core of 2-oxo-1,6-diazobicyclo[4.3.0]nonane-9-carboxylate-based peptidomimetics starting from ( S)-phenylalanine

A diastereoseletvive synthesis of a peptidic tetrahydropyridazinone 10 from ( S)-phenylalanine is reported. This derivative was then converted to the bicyclic peptidomimetic 11 , an important class of β-strand mimetic. A diastereoselective synthesis of the tetrahydropyridazinone A , an important com...

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Bibliographic Details
Published in:Tetrahedron letters 2003-05, Vol.44 (22), p.4227-4230
Main Authors: Gardiner, James, Abell, Andrew D.
Format: Article
Language:English
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Summary:A diastereoseletvive synthesis of a peptidic tetrahydropyridazinone 10 from ( S)-phenylalanine is reported. This derivative was then converted to the bicyclic peptidomimetic 11 , an important class of β-strand mimetic. A diastereoselective synthesis of the tetrahydropyridazinone A , an important component of β-strand mimetics, is presented based upon a stereoselective allylation of the ( S)-phenylalanine derived oxazolidinone B , followed by methanolysis of the oxazolidinone, ozonolysis, hydrazone formation and finally NaB(CN)H 3 reduction.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)00882-7