title: Divergent reactivity of an indole glucosinolate yields Lossen or Neber rearrangement products: the phytoalexin rapalexin A or a unique β-d-glucopyranose fused heterocycle.
abstract: Transformation of 1-t-Boc-4-methoxyindole-3-glucosinolate under acidic conditions yielded the potent phytoalexin rapalexin A, providing its first biomimetic synthesis via Lossen type rearrangement, while a novel 1-thioimidocarbonyl-β-d-glucopyranose heterocyclic system was obtained under basic conditions via Neber type rearrangement.
authors.affiliation: Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada. s.pedras@usask.ca.
authors.forename: M S C
authors.initials: MS
authors.lastname: Pedras
authors.forename: Q H
authors.initials: QH
authors.lastname: To
authors.forename: G
authors.initials: G
authors.lastname: Schatte
mesh_terms: D005961:Glucosinolates / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D013058:Mass Spectrometry; D009005:Monosaccharides / Q000737:chemistry*
chemical_list: C000611353:1-thioimidocarbonyl-beta-D-glucopyanose; D005961:Glucosinolates; D006571:Heterocyclic Compounds; D007211:Indoles; D017879:Isothiocyanates; D009005:Monosaccharides; C518225:rapalexin A