Redox-Neutral Dearomative Spirocyclization of Isoxazoline N-Oxides: A Route to Structural Analogs of Tyrosine-Derived Sponge Metabolites

Redox-Neutral Dearomative Spirocyclization of Isoxazoline N-Oxides: A Route to Structural Analogs of Tyrosine-Derived Sponge Metabolites Full article

Journal

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

Output data

Year: 2025, Volume: 90, Number: 40, Pages: 14322–14327 Pages count : DOI: 10.1021/acs.joc.5c01669

Authors

Malykhin Roman S. ¹ , Nguyen Duc Huy ^2,1 , Sukhorukov Alexey Yu. ¹

Affiliations

1	Laboratory of Organic and Metal-Organic Nitrogen-Oxygen Systems (LOMONOS), N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect, 47, Moscow 119991, Russian Federation
2	D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, Moscow 125047, Russian Federation

A novel synthetic route to spirocyclic isoxazolines based on a redox-neutral dearomative cyclization of 3-benzyl-substituted isoxazoline N-oxides has been developed. The reaction likely proceeds through isoxazoline ring opening with generation of an unstable N-oxoiminium cation. The latter acts as an O-electrophile in the cyclization involving the ipso-position of the aryl ring. The reaction exhibits a broad substrate scope and affords spirocyclic isoxazolines featuring novel substitution patterns compared with those accessible by synthetic methods or found in natural sources.

Malykhin R.S. , Nguyen D.H. , Sukhorukov A.Y.
Redox-Neutral Dearomative Spirocyclization of Isoxazoline N-Oxides: A Route to Structural Analogs of Tyrosine-Derived Sponge Metabolites
Journal of Organic Chemistry. 2025. V.90. N40. P.14322–14327. DOI: 10.1021/acs.joc.5c01669 WOS Scopus OpenAlex

Web of science:	WOS:001585266200001
Scopus:	2-s2.0-105018465925
OpenAlex:	W4414706793

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