Synthesis of PDE IVb Inhibitors. 3. Synthesis of (+)-, (−)-, and (±)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one via Reductive Domino Transformations of 3-β-Carbomethoxyethyl-Substituted Six-Membered Cyclic Nitronatesстатья
Статья опубликована в высокорейтинговом журнале
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Дата последнего поиска статьи во внешних источниках: 19 сентября 2017 г.
Аннотация:Simple three-step asymmetric and racemic syntheses of GlaxoSmithKline’s highly potent PDE IVb inhibitor 1 were developed. The suggested approach is based on reductive domino transformations of 3-β-carbomethoxyethyl-substituted six-membered cyclic nitronates, which are easily accessed by a stereoselective [4 + 2] cycloaddition of an appropriate nitroalkene to vinyl ethers. In vitro studies of PDE IVb inhibition by enantiomeric pyrrolizidinones (+)-1 and (−)-1 were performed.