title: Total synthesis of stephanotic acid methyl ester.
abstract: [structure: see text]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.
authors: Department of Chemistry, University of Exeter, UK.
authors: David J
authors: DJ
authors: Bentley
authors: Alexandra M Z
authors: AM
authors: Slawin
authors: Christopher J
authors: CJ
authors: Moody