title: A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues.
abstract: A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A and its analogues.
authors.affiliation: School of Pharmacy, Centre for Biomolecular Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK. weng.chan@nottingham.ac.uk.
authors.forename: Chou-Hsiung
authors.initials: CH
authors.lastname: Chen
authors.forename: Sivaneswary
authors.initials: S
authors.lastname: Genapathy
authors.forename: Peter M
authors.initials: PM
authors.lastname: Fischer
authors.forename: Weng C
authors.initials: WC
authors.lastname: Chan
mesh_terms: D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D010456:Peptides, Cyclic; C530877:argyrin A; D014364:Tryptophan