Synthesis of (2S,3S)-β-methyltryptophan

Guoxia Han, Arwel Lewis, Victor J Hruby

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Nα-Fmoc-protected (2S,3S)-β-methyltryptophan has been synthesized by asymmetric synthesis through the aid of an oxazolidinone auxiliary. Coupling of the mixed anhydride of Nin-Boc-protected indoleacrylic acid to the oxazolidinone auxiliary was achieved by lithium bromide and N,N-dimethylpyridine (DMAP). This reaction is milder and more convenient to run than the traditional conditions using butyl lithium.

Original languageEnglish (US)
Pages (from-to)4601-4603
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number28
DOIs
StatePublished - Jul 9 2001

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Oxazolidinones
Anhydrides
Lithium
indoleacrylic acid
lithium bromide

Keywords

  • β-methyltryptophan
  • Auxiliary assisted asymmetric synthesis
  • Constrained amino acids
  • Lithium bromide (LiBr)
  • N,N-dimethylaminopyridine (DMAP)

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of (2S,3S)-β-methyltryptophan. / Han, Guoxia; Lewis, Arwel; Hruby, Victor J.

In: Tetrahedron Letters, Vol. 42, No. 28, 09.07.2001, p. 4601-4603.

Research output: Contribution to journalArticle

Han, Guoxia ; Lewis, Arwel ; Hruby, Victor J. / Synthesis of (2S,3S)-β-methyltryptophan. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 28. pp. 4601-4603.
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