The Synthesis of 2,5-Dioxaspiro[3.4]octane Building Blocks: Three-Dimensional Spirocyclic Analogs of 1,4-Dioxanes
A ring-closing metathesis (RCM) strategy was employed for the synthesis of spirooxetane compounds with a tetrahydrofuran (THF) core. The approach proposed relied on the preparation of an unsaturated spirooxetane from vinyl oxetanol. The reaction sequence involved the NaH-mediated О-alkylation with m...
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| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
National University of Pharmacy (Kharkiv)
2025-04-01
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| Series: | Журнал органічної та фармацевтичної хімії |
| Subjects: | |
| Online Access: | https://ophcj.nuph.edu.ua/article/view/324901 |
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| Summary: | A ring-closing metathesis (RCM) strategy was employed for the synthesis of spirooxetane compounds with a tetrahydrofuran (THF) core. The approach proposed relied on the preparation of an unsaturated spirooxetane from vinyl oxetanol. The reaction sequence involved the NaH-mediated О-alkylation with methyl 2-(bromomethyl)acrylate in the presence of TBAI. The subsequent RCM reaction using the Grubbs’ II catalyst gave the dihydrofuran carboxylate with a yield of 70 %. The hydrogenation under high-pressure conditions using a Pearlman’s catalyst made it possible to obtain the saturated THF-derived carboxylate, which was then subjected to alkaline hydrolysis to give a stable lithium carboxylate. The corresponding alcohol obtained via LiAlH4-mediated reduction of the ester was oxidized to the corresponding aldehyde using DMP. The alcohol was further converted into a mesylate serving as a precursor for the corresponding amine and bromide. The set of dioxane analogs proposed can serve as promising building blocks readily available on a multigram scale for the scientific community. |
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| ISSN: | 2308-8303 2518-1548 |