Synthesis of PDE IVb Inhibitors. 1. Asymmetric Synthesis and Stereochemical Assignment of (+)- and (−)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one
Тип публикации: Journal Article
Дата публикации: 2011-09-16
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
21866916
Organic Chemistry
Краткое описание
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.
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Sukhorukov A. Yu. et al. 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. Vol. 76. No. 19. pp. 7893-7900.
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Sukhorukov A. Yu., 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. Vol. 76. No. 19. pp. 7893-7900.
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TY - JOUR
DO - 10.1021/jo201331h
UR - https://doi.org/10.1021/jo201331h
TI - Synthesis of PDE IVb Inhibitors. 1. Asymmetric Synthesis and Stereochemical Assignment of (+)- and (−)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one
T2 - Journal of Organic Chemistry
AU - Sukhorukov, Alexey Yu
AU - Boyko, Yaroslav D
AU - Ioffe, Sema L.
AU - Khomutova, Yulia A
AU - Nelyubina, Yulia V.
AU - Tartakovsky, Vladimir A
PY - 2011
DA - 2011/09/16
PB - American Chemical Society (ACS)
SP - 7893-7900
IS - 19
VL - 76
PMID - 21866916
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2011_Sukhorukov,
author = {Alexey Yu Sukhorukov and Yaroslav D Boyko and Sema L. Ioffe and Yulia A Khomutova and Yulia V. Nelyubina and Vladimir A Tartakovsky},
title = {Synthesis of PDE IVb Inhibitors. 1. Asymmetric Synthesis and Stereochemical Assignment of (+)- and (−)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one},
journal = {Journal of Organic Chemistry},
year = {2011},
volume = {76},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/jo201331h},
number = {19},
pages = {7893--7900},
doi = {10.1021/jo201331h}
}
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Sukhorukov, Alexey Yu., et al. “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, vol. 76, no. 19, Sep. 2011, pp. 7893-7900. https://doi.org/10.1021/jo201331h.