Stereoselective, solid phase-based synthesis of trans 3-alkyl-substituted β-lactams as analogues of cholesterol absorption inhibitors

A straightforward solid phase-based strategy for the rapid generation of two small libraries of trans 3-alkyl-substituted β-lactams is described. For the glycine-derived library, a controlled excess of nonactivated acid chlorides was used to prevent oxazinone formation. The second library involved t...

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Bibliographic Details
Published in:Tetrahedron 2012-12, Vol.68 (52), p.10780-10786
Main Authors: Delpiccolo, Carina M.L., Testero, Sebastián A., Leyes, Federico N., Boggián, Dora B., Camacho, Cristián M., Mata, Ernesto G.
Format: Article
Language:English
Subjects:
Beta-lactam derivatives
Cholesterol absorption inhibitors
Solid-phase synthesis
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Summary:A straightforward solid phase-based strategy for the rapid generation of two small libraries of trans 3-alkyl-substituted β-lactams is described. For the glycine-derived library, a controlled excess of nonactivated acid chlorides was used to prevent oxazinone formation. The second library involved the attachment of Fmoc-protected p-aminophenol to Wang resin for the preparation of structurally-closed analogues of known cholesterol absorption inhibitors. This strategy allowed us to introduce diversity in the three variable positions of the β-lactam ring. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.01.072