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Asymmetric synthesis of the central tryptophan residue of stephanotic acid
Authors:Bentley David J  Moody Christopher J
Affiliation:Department of Chemistry, University of Exeter, Exeter, UK EX4 4QD.
Abstract: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.
Keywords:
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