Total synthesis of stephanotic acid methyl ester

D J Bentley, A M Z Slawin, C J Moody

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

The methyl ester of the naturally occurring macrocyclic pentapeptide stephanotic acid, containing an unusual beta-substituted alpha-amino acid with a tryptophan C-6 to leucine beta-carbon link, has been synthesized. The key steps include the formation of this amino acid through a thioxo-oxazolidine intermediate and a Horner-Wadsworth-Emmons reaction using a phosphonoglycine, derived by a dirhodium(II)-catalyzed N-H insertion reaction, to give a dehydroamino acid and subsequent rhodium(I)-catalyzed asymmetric hydrogenation to introduce the modified tryptophan residue.

Original languageEnglish
Pages (from-to)1975-1978
Number of pages4
JournalOrganic Letters
Volume8
DOIs
Publication statusPublished - 11 May 2006

Keywords

  • ENANTIOSELECTIVE HYDROGENATION REACTIONS
  • ANTIMITOTIC BICYCLIC PEPTIDES
  • CENTRAL TRYPTOPHAN RESIDUE
  • CELOSIA-ARGENTEA
  • AMINO-ACIDS
  • ASYMMETRIC-SYNTHESIS
  • LAPORTEA-MOROIDES
  • CYCLIC PEPTIDE
  • SEEDS
  • DERIVATIVES

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