A chiral synthesis of (-)-spiro[1-azabicyclo[2.2.2]octane-3,5'- oxazolidin-2'-one]: a conformationally restricted analogue of acetylcholine that is a potent and selective alpha7 nicotinic receptor agonist

A direct, short chiral synthesis of the selective alpha7 nicotinic receptor agonist (-)-spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (AR-R17779) is presented. The key step utilized attack of the dianion of the (R)-HYTRA ester [(R)-(+)-2-hydroxy-1,2,2-triphenylethyl acetate] on q...

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Veröffentlicht in:	Journal of organic chemistry 2004-09, Vol.69 (19), p.6493-6495
Hauptverfasser:	Macor, John E, Mullen, George, Verhoest, Patrick, Sampognaro, Anthony, Shepardson, Bruce, Mack, Robert A
Format:	Artikel
Sprache:	eng
Schlagworte:	Bridged-Ring Compounds - chemical synthesis Bridged-Ring Compounds - chemistry Bridged-Ring Compounds - pharmacology Magnetic Resonance Spectroscopy Molecular Structure Nicotinic Agonists - chemical synthesis Nicotinic Agonists - chemistry Nicotinic Agonists - pharmacology Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Spiro Compounds - pharmacology Stereoisomerism
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Zusammenfassung:	A direct, short chiral synthesis of the selective alpha7 nicotinic receptor agonist (-)-spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (AR-R17779) is presented. The key step utilized attack of the dianion of the (R)-HYTRA ester [(R)-(+)-2-hydroxy-1,2,2-triphenylethyl acetate] on quinuclidin-3-one, followed by a selective precipitation of the diasteriomeric tertiary alcohol that led to (S)-(-)-AR-R17779 in two additional steps.
ISSN:	0022-3263