Asymmetric synthesis of the central tryptophan residue of stephanotic acid.
The C-6 substituted tryptophan di- and tri-peptides and , representing the tryptophan core of stephanotic acid, have been synthesized, the key steps being the formation of the phosphono-di- and tri-peptides and by a highly chemoselective rhodium(II) catalyzed carbene N-H insertion reaction, their subsequent Horner-Wadsworth-Emmons reactions with N-Boc-6-bromoindole-3-carboxaldehyde, and the rhodium(I) catalyzed asymmetric hydrogenation of the resulting dehydro di- and tri-peptides.
Bentley
David J
DJ
Department of Chemistry, University of Exeter, Exeter, UK EX4 4QD.
Moody
Christopher J
CJ
D002384:Catalysis; D006865:Hydrogenation; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D014364:Tryptophan / Q000138:chemical synthesis / Q000737:chemistry*
D010455:Peptides; D010456:Peptides, Cyclic; C409632:stephanotic acid; D014364:Tryptophan; D012238:Rhodium