A general strategy for the synthesis of azapeptidomimetic lactams |
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Authors: | Robert L. Broadrup |
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Affiliation: | Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA 19010-2899, USA |
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Abstract: | A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/homologated serine-azaalanine derivatives. These include sterically-congested β-lactams, as well as γ-butyrolactam and δ-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding α-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. |
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Keywords: | Peptidomimetic Lactams Azapeptide Mitsunobu reaction |
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