ArticleThe Journal of organic chemistry2024
Insight into the Course of the Ferrier Rearrangement Used to Obtain Untypical Diosgenyl Saponins.
Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Thermodynamic stability and anticancer activity of 2,3-unsaturated and 2,3-dideoxy OScientific reports · 2026Article
- Synergistic Gold-Silicon Catalysis: Unravelling Alkynyl Gold Reactivity and Application to the High-Performance C-Alkynylation of Glycals.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
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10 authors.
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Abstract
The Ferrier rearrangement was utilized to obtain 2,3-unsaturated diosgenyl glycosides. This reaction proceeded with high stereoselectivity, yielding mostly saponins with an α configuration (hexoses) or predominantly with a β configuration (pentoses). The diversity of the glycals used and the glycosides obtained enabled a deep discussion of the Ferrier rearrangement mechanism. The mechanism was supported by DFT calculations concerning the intermediate ions. It was concluded that the vinylogous anomeric effect may influence the reactivity of the glycals. Two possible Ferrier rearrangement intermediates, dioxolenium and allyloxycarbenium ions, were hypothesized to exist in thermodynamic equilibrium that shifted toward the former. The allyloxycarbenium ion participates in the final rearrangement step and determines the reaction regioselectivity. Furthermore, the conformational stability of the 2,3-unsaturated pyranose ring determines the stereoselectivity of the reaction. Factors influencing this stability, as well as the NMR data enabling recognition of the
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