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 α7 nicotinic receptor agonist

被引：27

作者：

Macor, JE ^{[1
]}

Mullen, G ^{[1
]}

Verhoest, P ^{[1
]}

Sampognaro, A ^{[1
]}

Shepardson, B ^{[1
]}

Mack, RA ^{[1
]}

机构：

[1] AstraZeneca, CNS Discovery, Wilmington, DE 19850 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 19期

关键词：

D O I：

10.1021/jo049404q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct, short chiral synthesis of the selective 0 nicotinic receptor agonist (-)-spiro[l-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.

引用

页码：6493 / 6495

页数：3

共 15 条

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