Synthesis of (-)-Epibatidine and Its Derivatives from Chiral Allene-1,3-dicarboxylate Esters
| Autor: | Toshio Fujiwara, Hiroyuki Kimura, Takahiro Katoh, Kiyoharu Nishide, Manabu Node, Tetsuya Kajimoto |
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| Rok vydání: | 2006 |
| Předmět: |
Magnetic Resonance Spectroscopy
Spectrophotometry Infrared Pyridines Stereochemistry Allene Receptors Nicotinic Spectrometry Mass Fast Atom Bombardment chemistry.chemical_compound Drug Discovery medicine Dicarboxylic Acids Nicotinic Agonists Acetylcholine receptor Chemistry Diastereomer Enantioselective synthesis Esters General Chemistry General Medicine Nuclear magnetic resonance spectroscopy Fast atom bombardment Bridged Bicyclo Compounds Heterocyclic Single isomer Alkadienes Nicotinic agonist Epibatidine Central nerve system Indicators and Reagents medicine.drug |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 54:399-402 |
| ISSN: | 1347-5223 0009-2363 |
| Popis: | (-)-Epibatidine, an excellent candidate of non-opioidal anesthesia, was formally synthesized in short steps from di-(l)-menthyl (R)-allene-1,3-dicarboxylate that was facilely prepared as a single isomer by means of crystallization-induced asymmetric transformation from a diastereomer mixture of (R)- and (S)-allene-1,3-dicarboxylates. Taking advantage of the chiral synthesis, derivatives of (-)-epibatidine were also prepared for targeting diagnostic agents that could bind nicotinic acetylcholine receptors (nAChRs) in the mammalian central nerve system. |
| Databáze: | OpenAIRE |
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