Expedient solid-phase synthesis of putative β-turn mimetics incorporating the i + 1, i + 2, and i + 3 sidechains

Alex A. Virgilio, Stephan C Schuerer, Jonathan A. Ellman

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

A number of putative β-turn mimetics that incorporate sidechain functionality at the i + 1, i + 2, and i + 3 positions were synthesized on solid support in high levels of purity and in good overall yields from readily available starting materials. A variety of sidechain functionality, ring sizes, and sidechain stereochemistries were introduced demonstrating the generality of the synthesis method. A significant feature of the synthesis sequence is the use of guanidine resin that functions as both a solid-phase extraction resin and a support-bound general base catalyst.

Original languageEnglish
Pages (from-to)6961-6964
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number39
DOIs
StatePublished - Sep 23 1996
Externally publishedYes

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Solid-Phase Synthesis Techniques
Guanidine
Solid Phase Extraction
Resins
Stereochemistry
Catalyst supports
Catalysts

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Expedient solid-phase synthesis of putative β-turn mimetics incorporating the i + 1, i + 2, and i + 3 sidechains. / Virgilio, Alex A.; Schuerer, Stephan C; Ellman, Jonathan A.

In: Tetrahedron Letters, Vol. 37, No. 39, 23.09.1996, p. 6961-6964.

Research output: Contribution to journalArticle

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