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Synthesis of PDE IVb Inhibitors. 1. Asymmetric Synthesis and Stereochemical Assignment of (+)- and (−)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one Научная публикация

Журнал Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263
Вых. Данные Год: 2011, Том: 76, Номер: 19, Страницы: 7893-7900 Страниц : 8 DOI: 10.1021/jo201331h
Авторы Sukhorukov Alexey Yu. 1 , Boyko Yaroslav D. 1 , Ioffe Sema L. 1 , Khomutova Yulia A. 1 , Nelyubina Yulia V. 2 , Tartakovsky Vladimir A. 1
Организации
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prosp. 47, Moscow, Russian Federation
2 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilov str. 28, Moscow, Russian Federation

Реферат: Asymmetric synthesis of GlaxoSmithKline’s highly potent phosphodiesterase inhibitor 1 has been accomplished in nine steps and 16% overall yield. The original strategy suggested involves as a key step the silylation of enantiopure six-membered cyclic nitronates 4 obtained by a highly stereoselective [4 + 2]-cycloaddition of an appropriate nitroalkene 5 to trans-1-phenyl-2-(vinyloxy)cyclohexane. Functionalization of the resulting 5,6-dihydro-4H-1,2-oxazine and subsequent stereoselective reduction of 1,2-oxazine ring in intermediate 2 furnished the pyrrolizidinone framework with the recovery of chiral auxiliary alcohol.
Библиографическая ссылка: Sukhorukov A.Y. , Boyko Y.D. , Ioffe S.L. , Khomutova Y.A. , Nelyubina Y.V. , Tartakovsky V.A.
Synthesis of PDE IVb Inhibitors. 1. Asymmetric Synthesis and Stereochemical Assignment of (+)- and (−)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one
Journal of Organic Chemistry. 2011. V.76. N19. P.7893-7900. DOI: 10.1021/jo201331h WOS Scopus OpenAlex
Идентификаторы БД:
Web of science: WOS:000295302300025
Scopus: 2-s2.0-80054103755
OpenAlex: W2321417166
Цитирование в БД:
БД Цитирований
OpenAlex 24
Scopus 26
Web of science 22
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