889942-79-4Relevant articles and documents
Divergent reactivity of an indole glucosinolate yields Lossen or Neber rearrangement products: The phytoalexin rapalexin A or a unique β-d-glucopyranose fused heterocycle
Pedras,To,Schatte
supporting information, p. 2505 - 2508 (2016/02/18)
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.
The first isocyanide of plant origin expands functional group diversity in cruciferous phytoalexins: Synthesis, structure and bioactivity of isocyalexin A
Pedras, M. Soledade C.,Yaya, Estifanos E.
supporting information; experimental part, p. 3613 - 3616 (2012/06/18)
Although isocyanides are not rare amongst terrestrial microbes and marine organisms, despite tens of thousands of natural products isolated from plants, isocyanides are still missing. Isocyalexin A is the first isocyanide of plant origin. Isocyalexin A was isolated from UV-irradiated rutabaga roots and shown to be a new cruciferous phytoalexin. Its chemical structure was proven by analysis of NMR spectroscopic data and chemical synthesis.