Synthesis of (4R)-4-Ethenyl-5,5-dimethyltetrahydrofuran-2-one and 6,6-Dimethyl-5-(2-oxopropyl)tetrahydro-2H-pyran-2-one from (+)-3-Carene

Oxidative cleavage of (+)-3-carene gave vicinal disubstituted dimethylcyclopropane α,ω-amido- and ketoesters, and intramolecular cyclization of the latter by the action of methanesulfonic acid afforded (4R)-4-ethenyl-5,5-dimethyltetrahydrofuran-2-one and 6,6-dimethyl-5-(2-oxopropyl)tetrahydro-2H-pyran-2-one.

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Publication Details

Journal
Russian Journal of Organic Chemistry
Published
2025-10-01
DOI
https://doi.org/10.1134/s1070428025603085
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Synthesis of (4R)-4-Ethenyl-5,5-dimethyltetrahydrofuran-2-one and 6,6-Dimethyl-5-(2-oxopropyl)tetrahydro-2H-pyran-2-one from (+)-3-Carene

N. A. Ivanova, G. A. Shavaleeva, M. S. Miftakhov
Russian Journal of Organic Chemistry
Catalytic Alkyne Reactions
article

Synthesis of (4R)-4-Ethenyl-5,5-dimethyltetrahydrofuran-2-one and 6,6-Dimethyl-5-(2-oxopropyl)tetrahydro-2H-pyran-2-one from (+)-3-Carene

N. A. Ivanova, G. A. Shavaleeva, M. S. Miftakhov
article en

Abstract

Oxidative cleavage of (+)-3-carene gave vicinal disubstituted dimethylcyclopropane α,ω-amido- and ketoesters, and intramolecular cyclization of the latter by the action of methanesulfonic acid afforded (4R)-4-ethenyl-5,5-dimethyltetrahydrofuran-2-one and 6,6-dimethyl-5-(2-oxopropyl)tetrahydro-2H-pyran-2-one.

Russian Journal of Organic ChemistryVol. 61(10)
Ufa Institute of Chemistry (RU)
Openalex Percentile: Top 34%
Catalytic Alkyne Reactions
DOISourceOpenAlex
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Synthesis of (4R)-4-Ethenyl-5,5-dimethyltetrahydrofuran-2-one and 6,6-Dimethyl-5-(2-oxopropyl)tetrahydro-2H-pyran-2-one from (+)-3-Carene — N. A. Ivanova, G. A. Shavaleeva, et al. · Russian Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS