889678-85-7Relevant academic research and scientific papers
Total synthesis of stephanotic acid methyl ester
Bentley, David J.,Slawin, Alexandra M. Z.,Moody, Christopher J.
, p. 1975 - 1978 (2007/10/03)
The methyl ester of the naturally occurring macrocyclic pentapeptide stephanotic acid, containing an unusual β-substituted α-amino acid with a tryptophan C-6 to leucine β-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.
