Total asymmetric synthesis of highly constrained amino acids β-isopropyl-2',6'-dimethyl-tyrosines

Yinglin Han, Subo Liao, Wei Qiu, Chaozhong Cai, Victor J. Hruby

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

All four stereoisomers of the highly constrained aromatic α-amino acid β-isopropyl-2',6'-dimethyltyrosine have been asymmetrically synthesis on a large scale. A catalytic asymmetric Michael addition of an organocuprate to a chiral α,β-unsaturated acyloxazolidinone and subsequent direct or indirect stereoselective electrophilic azidation of the α-position of the resulting product was followed by hydrolysis, hydrogenation and finally deprotection of the phenol group to afford the desired amino acids. The reactions generally proceeded in good stereoselectivities (75-95% ee/de) and yields (70-90%), making these optically pure amino acids available in large scale practical for the synthesis of peptides and other studies.

Original languageEnglish (US)
Pages (from-to)5135-5138
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number29
DOIs
StatePublished - Jul 21 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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