Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones

Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones Full article

Journal

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

Output data

Year: 2024, Volume: 89, Number: 1, Pages: 379-394 Pages count : 16 DOI: 10.1021/acs.joc.3c02154

Authors

Okladnikov Ilya V. ^1,2 , Aksenova Svetlana A. ^3,4 , Ioffe Sema L. ² , Sukhorukov Alexey Yu. ²

Affiliations

1	D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, 125047 Moscow, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect, 47, 119991 Moscow, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova str. 28, 119991 Moscow, Russian Federation
4	Moscow Institute of Physics and Technology (National Research University), Institutskiy per. 9, Dolgoprudny, 141700 Moscow Region, Russian Federation

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.

Okladnikov I.V. , Aksenova S.A. , Ioffe S.L. , Sukhorukov A.Y.
Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones
Journal of Organic Chemistry. 2024. V.89. N1. P.379-394. DOI: 10.1021/acs.joc.3c02154 WOS Scopus OpenAlex

Web of science:	WOS:001137551300001
Scopus:	2-s2.0-85182429616
OpenAlex:	W4389765129

DB	Citing
OpenAlex	7
Scopus	5
Web of science	6