Divergent reactivity of an indole glucosinolate yields Lossen or Neber rearrangement products: the phytoalexin rapalexin A or a unique β-d-glucopyranose fused heterocycle?
Chemical Communications Pub Date: 2015-12-24 DOI: 10.1039/C5CC09822J
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.
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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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