Total synthesis of stephanotic acid methyl ester.

@article{Bentley2006TotalSO,
  title={Total synthesis of stephanotic acid methyl ester.},
  author={D. Bentley and A. M. Slawin and C. Moody},
  journal={Organic letters},
  year={2006},
  volume={8 10},
  pages={
          1975-8
        }
}
  • D. Bentley, A. M. Slawin, C. Moody
  • Published 2006
  • Medicine, Chemistry
  • Organic letters
  • [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… CONTINUE READING
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