Synthesis of Bispidine–Isoxazolidine-Fused Multicyclic Scaffolds via Nitrone [3+2] Cycloaddition: Toward “Hetero-Lupine Alkaloids”

Synthesis of Bispidine–Isoxazolidine-Fused Multicyclic Scaffolds via Nitrone [3+2] Cycloaddition: Toward “Hetero-Lupine Alkaloids” Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2026, DOI: 10.1021/acs.orglett.6c02883

Authors

Liklikadze Georgy K. ¹ , Medved’ko Aleksei V. ¹ , Simonyan Grigory S. ^2,1 , Mirakbarov Mirumid H. ¹ , Vatsadze Sergey Z. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation
2	Lomonosov Moscow State University, Department of Chemistry, Moscow 119991, Russian Federation

We present a highly efficient strategy for the assembly of bispidine−isoxazolidine-fused multicyclic structures via [3+2] cycloaddition of alkenes to a nitrone-functionalized bispidine framework. The reaction smoothly delivers diverse hybrid heterocycles featuring complex stereochemistry at the isoxazolidine−bispidine junction point in high yields and good selectivity. This approach opens a straightforward pathway to new synthetic analogues of natural compounds (primarily lupine alkaloids) and may prove to be useful for the discovery of new bioactive molecules and ligands for catalysis.

Liklikadze G.K. , Medved’ko A.V. , Simonyan G.S. , Mirakbarov M.H. , Vatsadze S.Z.
Synthesis of Bispidine–Isoxazolidine-Fused Multicyclic Scaffolds via Nitrone [3+2] Cycloaddition: Toward “Hetero-Lupine Alkaloids”
Organic Letters. 2026. DOI: 10.1021/acs.orglett.6c02883 WOS Scopus OpenAlex

Submitted:	Jul 1, 2026
Accepted:	Sep 2, 2026
Published online:	Sep 7, 2026

≡ Web of science:	WOS:001870779900001
≡ Scopus:	2-s2.0-105051047759
≡ OpenAlex:	W7211867890