Rapid generation of cis-constrained norstatine analogs using a TMSN3-modified Passerini MCC/N-capping strategy

Thomas Nixey, Christopher Hulme

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

A novel application of the TMSN3-modified Passerini three-component reaction is disclosed for the rapid solution phase synthesis of cis constrained norstatine mimetic libraries. The reaction of an N-BOC-α-amino aldehyde, an isocyanide and trimethylsilylazide in dichloromethane, followed by deprotection and N-capping with TFP esters affords cis constrained norstatine mimetics. This efficient protocol, producing products with three diversity points, can be used to generate arrays of biologically relevant small molecules for protease targeted screening.

Original languageEnglish (US)
Pages (from-to)6833-6835
Number of pages3
JournalTetrahedron Letters
Volume43
Issue number38
DOIs
StatePublished - Sep 16 2002
Externally publishedYes

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Methylene Chloride
Cyanides
Aldehydes
Libraries
Screening
Esters
Peptide Hydrolases
Molecules
3-amino-2-hydroxy-5-methylhexanoic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Rapid generation of cis-constrained norstatine analogs using a TMSN3-modified Passerini MCC/N-capping strategy. / Nixey, Thomas; Hulme, Christopher.

In: Tetrahedron Letters, Vol. 43, No. 38, 16.09.2002, p. 6833-6835.

Research output: Contribution to journalArticle

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