title: Synthesis of fully protected, reverse N-prenylated (2S,3R)-3-hydroxytryptophan, a unique building block of the cyclomarins.
abstract: Reverse N-prenylated 3-hydroxytryptophan, the rather exotic amino acid of the cyclomarins, is obtained in enantio- and diastereomerically pure and fully protected form by a combination of a highly stereoselective addition of a zincated indole toward protected serinal and subsequent palladium-catalyzed N-prenylation.
authors.affiliation: Institute of Organic Chemistry, Saarland University, P.O. Box 151150, 66041 Saarbrücken, Germany. u.kazmaier@mx.uni-saarland.de.
authors.forename: Philipp
authors.initials: P
authors.lastname: Barbie
authors.forename: Uli
authors.initials: U
authors.lastname: Kazmaier
mesh_terms: D006916:5-Hydroxytryptophan / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D009842:Oligopeptides / Q000737:chemistry*; D054876:Prenylation
chemical_list: D009842:Oligopeptides; D006916:5-Hydroxytryptophan