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52. Synthesis of Forsythenethoside A, a Neuroprotective Macrocyclic Phenylethanoid Glycoside, and NMR Analysis of Conformers

Author

Biao Yu, Antonio Molinaro, Alba Silipo, Zhifei Hu, Wei Li, Hu, Zhifei, Silipo, Alba, Li, Wei, Molinaro, Antonio, and Yu, Biao

Subjects
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
Abstract

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.

Published
2019

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