Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones
Publication type: Journal Article
Publication date: 2023-12-14
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
38096381
Organic Chemistry
Abstract
Pyrrolizidine is among the saturated N-heterocyclic scaffolds most frequently found in natural products and pharmaceutically relevant substances. Herein, a strategy for the synthesis of polysubstituted pyrrolizidine-3-ones by catalytic reductive domino-type recyclization of properly functionalized isoxazoline N-oxides was developed. The process is diastereoselective, and one diastereomer (out of four possible ones) is predominant in many of the studied cases. Using the developed method, modifications of potent GSK's PDE4 inhibitor and MSD's potent hNK1 antagonist were prepared.
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Okladnikov I. V. et al. Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones // Journal of Organic Chemistry. 2023. Vol. 89. No. 1. pp. 379-394.
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Okladnikov I. V., Aksenova S. A., Ioffe S. L., Sukhorukov A. Yu. Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones // Journal of Organic Chemistry. 2023. Vol. 89. No. 1. pp. 379-394.
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TY - JOUR
DO - 10.1021/acs.joc.3c02154
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c02154
TI - Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones
T2 - Journal of Organic Chemistry
AU - Okladnikov, Ilya V.
AU - Aksenova, Svetlana A.
AU - Ioffe, Sema L.
AU - Sukhorukov, Alexey Yu
PY - 2023
DA - 2023/12/14
PB - American Chemical Society (ACS)
SP - 379-394
IS - 1
VL - 89
PMID - 38096381
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2023_Okladnikov,
author = {Ilya V. Okladnikov and Svetlana A. Aksenova and Sema L. Ioffe and Alexey Yu Sukhorukov},
title = {Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {89},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c02154},
number = {1},
pages = {379--394},
doi = {10.1021/acs.joc.3c02154}
}
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MLA
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Okladnikov, Ilya V., et al. “Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones.” Journal of Organic Chemistry, vol. 89, no. 1, Dec. 2023, pp. 379-394. https://pubs.acs.org/doi/10.1021/acs.joc.3c02154.
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