title: Indole prenylation in alkaloid synthesis.
abstract: Important biologically active indole alkaloids are decorated with prenyl (3,3-dimethylallyl) and tert-prenyl (1,1-dimethylallyl) groups. Covering the literature until the end of 2010, this review article comprehensively summarises and discusses the currently available technologies of prenylation and tert-prenylation of indoles, which have been applied in natural products total syntheses or could be applied there in the near future. We focus on those procedures which introduce the C(5) units in one step, organised according to the indole position to be functionalised. Key strategies include electrophilic and nucleophilic prenylation and tert-prenylation, prenyl and tert-prenyl rearrangements, transition metal-mediated reactions and enzymatic methods.
authors.affiliation: Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany. th.lindel@tu-bs.de
authors.forename: Thomas
authors.initials: T
authors.lastname: Lindel
authors.forename: Nils
authors.initials: N
authors.lastname: Marsch
authors.forename: Santosh Kumar
authors.initials: SK
authors.lastname: Adla
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D054876:Prenylation
chemical_list: D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; D026121:Indole Alkaloids; D007211:Indoles; C030374:indole