Facile and rapid route for the synthesis of novel norstatine analogs via PADAM-cyclization methodology

Arthur Y. Shaw, Federico Medda, Christopher Hulme

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The following report describes novel methodology for the rapid synthesis of unique conformationally constrained norstatine analogs of potential biological relevance. A PADAM (Passerini reaction-Amine Deprotection-Acyl Migration reaction) sequence is followed by a TFA-mediated microwave-assisted cyclization to generate the final benzimidazole isostere of the norstatine scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.

Original languageEnglish (US)
Pages (from-to)1313-1315
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number11
DOIs
StatePublished - Mar 14 2012

Fingerprint

Cyclization
Amines
Microwaves
Scaffolds
3-amino-2-hydroxy-5-methylhexanoic acid
benzimidazole

Keywords

  • Benzimidazole
  • Multicomponent reactions
  • Passerini reaction
  • Peptidomimetics
  • Protease inhibitor

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Facile and rapid route for the synthesis of novel norstatine analogs via PADAM-cyclization methodology. / Shaw, Arthur Y.; Medda, Federico; Hulme, Christopher.

In: Tetrahedron Letters, Vol. 53, No. 11, 14.03.2012, p. 1313-1315.

Research output: Contribution to journalArticle

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