Synthesis of Forsythenethoside A, a Neuroprotective Macrocyclic Phenylethanoid Glycoside, and NMR Analysis of Conformers
| Autor: | Biao Yu, Antonio Molinaro, Alba Silipo, Zhifei Hu, Wei Li |
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| Přispěvatelé: | Hu, Zhifei, Silipo, Alba, Li, Wei, Molinaro, Antonio, Yu, Biao |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Models
Molecular chemistry.chemical_classification Magnetic Resonance Spectroscopy 010405 organic chemistry Chemistry Stereochemistry Longest linear sequence Organic Chemistry Molecular Conformation Glycoside Chemistry Techniques Synthetic Nuclear magnetic resonance spectroscopy Phenylethanoid Phenylethyl Alcohol 010402 general chemistry 01 natural sciences Chemical synthesis 0104 chemical sciences chemistry.chemical_compound Neuroprotective Agents Intramolecular force Oxidative coupling of methane Glycosides Conformational isomerism |
| Popis: | Forsythenethoside A (1) is a structurally unique macrocyclic phenylethanoid glycoside, which was isolated from Forsynthia suspensa and displayed considerable neuroprotective activities. Here, we report its first chemical synthesis via a longest linear sequence of 14 steps in 5% overall yield wherein intramolecular oxidative coupling was successfully employed to realize the pivotal macrocyclization. NMR analysis revealed the existence of an unexpected conformational interconversion of the congested macrocycles. |
| Databáze: | OpenAIRE |
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