一种吲哚硫代葡萄糖苷的不同反应性产生洛森或内贝重排产物：植物抗毒素rapalexin A或一种独特的与β - d - 吡喃葡萄糖融合的杂环。
Divergent reactivity of an indole glucosinolate yields Lossen or Neber rearrangement products: the phytoalexin rapalexin A or a unique β-d-glucopyranose fused heterocycle.
作者信息
Pedras M S C, To Q H, Schatte G
机构信息
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada.
出版信息
Chem Commun (Camb). 2016 Feb 11;52(12):2505-8. doi: 10.1039/c5cc09822j. Epub 2016 Jan 7.
PMID:26740010
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.
摘要
1-叔丁氧羰基-4-甲氧基吲哚-3-硫代葡萄糖苷在酸性条件下转化生成强效植物抗毒素rapalexin A，通过洛森重排实现了其首次仿生合成，而在碱性条件下通过内伯重排得到了一种新型的1-硫代异羰基-β-D-吡喃葡萄糖杂环体系。
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