Synthesis and Stereochemical Assignment of Diastereomeric Steroidal Spiro-1,2,4-trioxolanes with Sitostanone Motif Using PLS2 Chemometric Analysis of DFT-Calculated and Experimental

Alexander Lobov, Anastasiya Kerimova, Irina Smirnova, Dmitriy Polovyanenko, Irina Bagryanskaya, Oxana Kazakova

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Article in Molecules (Basel, Switzerland), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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6 authors.

Alexander LobovUfa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71, pr. Oktyabrya, 450054 Ufa, Russia.ORCID 0000-0002-9223-508X

Anastasiya KerimovaUfa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71, pr. Oktyabrya, 450054 Ufa, Russia.ORCID 0000-0003-2910-6805

Irina SmirnovaUfa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71, pr. Oktyabrya, 450054 Ufa, Russia.ORCID 0000-0001-7176-505X

Dmitriy PolovyanenkoN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, 630090 Novosibirsk, Russia.

Irina BagryanskayaN. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, 630090 Novosibirsk, Russia.

Oxana KazakovaUfa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71, pr. Oktyabrya, 450054 Ufa, Russia.ORCID 0000-0002-5606-1588

Funding

Russian Science Foundation 25-23-00668

6 · The paper itself

Abstract

The synthesis and multi-step spectroscopic characterization of diastereomeric 3-spiro-1,2,4-trioxolanes obtained by Griesbaum co-ozonolysis of sitostanone O-methyl oxime with two types of fluorinated ketones are reported. The reaction furnished four possible diastereomers that differ in the α/β orientation of the peroxide bridge relative to the steroid A-ring and in the

Indexed as

3-spiro-1,2,4-trioxolanechemometricsDFTGriesbaum co-ozonolysishigh-resolution NMRsitostanonesteroidsX-ray analysis

Identifiers

PMID42738764

DOI10.3390/molecules31173105

PMCPMC13567592

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