title: Asymmetric synthesis of the highly methylated tryptophan portion of the hemiasterlin tripeptides.
abstract: [reaction: see text] The asymmetric synthesis of the methylated tryptophan portion of hemiasterlin peptides is described. The key reactions are a SnCl4-mediated ring opening of epoxynitriles or epoxysulfones by N-methylindole followed by an asymmetric Strecker reaction. A second approach involving opening of glycidic esters by indoles is also described.
authors.affiliation: Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.
authors.forename: Ranga
authors.initials: R
authors.lastname: Reddy
authors.forename: James B
authors.initials: JB
authors.lastname: Jaquith
authors.forename: Venugopal Rao
authors.initials: VR
authors.lastname: Neelagiri
authors.forename: Sherine
authors.initials: S
authors.lastname: Saleh-Hanna
authors.forename: Tony
authors.initials: T
authors.lastname: Durst
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D008745:Methylation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D009842:Oligopeptides; C467070:hemiasterlin; D014364:Tryptophan