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

Guoxia Han, Arwel Lewis, Victor J. Hruby

Research output: Contribution to journalArticle

28 Scopus citations

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

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of (2S, 3S)-β-methyltryptophan'. Together they form a unique fingerprint.

Cite this