TITLE

Synthesis of constrained aromatic β2,3,3-amino alcohol scaffolds — Precursors of non-proteinogenic phenylalanine for peptidomimetics

AUTHOR(S)
Bhella, Surinderjit Singh; Ishar, Mohan Paul S.; Singh, Gajendra; Singh, Rajinder; Singh, Gurpinder; Raj, Tilak
PUB. DATE
May 2008
SOURCE
Canadian Journal of Chemistry;May2008, Vol. 86 Issue 5, p451
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
ABSTRACT
Novel constrained β2,3,3-amino alcohol scaffolds (11a–11e) with varied substitution patterns have been synthesized by reductive cleavage of the N–O bond of isoxazolidines (10a–10e) derived from intramolecular 1,3-dipolar cycloadditions. A number of methods were probed for reductive cleavage, however, better results were obtained with ammonium formate in the presence of Pd/C or Zn as compared to Zn/acetic acid. The obtained scaffolds (11a–11e) can serve as valuable building blocks for peptidomimetics.
ACCESSION #
31801599

 

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