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 Nitronates

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 Nitronates Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2012, Volume: 77, Number: 12, Pages: 5465-5469 Pages count : 5 DOI: 10.1021/jo300955n

Authors

Sukhorukov Alexey Yu. ¹ , Boyko Yaroslav D. ¹ , Nelyubina Yulia V. ² , Gerard Stephane ³ , Ioffe Sema L. ¹ , Tartakovsky Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic#R#Chemistry, Russian Academy of Sciences, 119991, Leninsky prosp.#R#47, Moscow, Russia
2	A. N. Nesmeyanov Institute of Organoelement#R#Compounds, Russian Academy of Sciences, 119991,#R#Vavilov str., 28, Moscow, Russia
3	Institut de Chimie Moléculaire de Reims, UMR CNRS 6229, Université de Reims-Champagne-Ardenne, Faculté de Pharmacie, 51 rue Cognacq-Jay, F-51096 Reims Cedex, France

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.

Sukhorukov A.Y. , Boyko Y.D. , Nelyubina Y.V. , Gerard S. , Ioffe S.L. , Tartakovsky V.A.
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 Nitronates
Journal of Organic Chemistry. 2012. V.77. N12. P.5465-5469. DOI: 10.1021/jo300955n WOS Scopus OpenAlex

Web of science:	WOS:000305205400033
Scopus:	2-s2.0-84862544617
OpenAlex:	W2319011756

DB	Citing
OpenAlex	28
Scopus	29
Web of science	24