A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in <i>para</i>-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents
Two approaches to the synthesis of <i>para</i>-menthene epoxide ((1<i>S</i>,5<i>S</i>,6<i>R</i>)<i>-</i><b>4</b>) are developed. The first approach includes a reaction between chlorohydrin <b>7</b> and NaH in THF. Th...
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| Format: | Article |
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MDPI AG
2023-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/21/7303 |
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| author | Alexandra V. Podturkina Oleg V. Ardashov Konstantin P. Volcho Nariman F. Salakhutdinov |
| author_facet | Alexandra V. Podturkina Oleg V. Ardashov Konstantin P. Volcho Nariman F. Salakhutdinov |
| author_sort | Alexandra V. Podturkina |
| collection | DOAJ |
| description | Two approaches to the synthesis of <i>para</i>-menthene epoxide ((1<i>S</i>,5<i>S</i>,6<i>R</i>)<i>-</i><b>4</b>) are developed. The first approach includes a reaction between chlorohydrin <b>7</b> and NaH in THF. The second involves the formation of epoxide in the reaction of corresponding diacetate <b>6</b> with sodium <i>tert</i>-butoxide. One possible mechanism of this reaction is proposed to explain unexpected outcomes in the regio- and stereospecificity of epoxide (1<i>S</i>,5<i>S</i>,6<i>R</i>)<i>-</i><b>4</b> formation. The epoxide ring in (1<i>S</i>,5<i>S</i>,6<i>R</i>)<i>-</i><b>4</b> is then opened by various <i>S</i>- and <i>O</i>-nucleophiles. This series of reactions allows for the stereoselective synthesis of diverse derivatives of the monoterpenoid Prottremine <b>1</b>, a compound known for its antiparkinsonian activity, including promising antiparkinsonian properties. |
| first_indexed | 2024-03-11T11:25:12Z |
| format | Article |
| id | doaj.art-42761dd70790437f9c4208c51a980431 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T11:25:12Z |
| publishDate | 2023-10-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-42761dd70790437f9c4208c51a9804312023-11-10T15:08:33ZengMDPI AGMolecules1420-30492023-10-012821730310.3390/molecules28217303A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in <i>para</i>-Mentha-1,2-diol in the Search for New Antiparkinsonian AgentsAlexandra V. Podturkina0Oleg V. Ardashov1Konstantin P. Volcho2Nariman F. Salakhutdinov3Department of Medicinal Chemistry, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentiev Ave. 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentiev Ave. 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentiev Ave. 9, 630090 Novosibirsk, RussiaDepartment of Medicinal Chemistry, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentiev Ave. 9, 630090 Novosibirsk, RussiaTwo approaches to the synthesis of <i>para</i>-menthene epoxide ((1<i>S</i>,5<i>S</i>,6<i>R</i>)<i>-</i><b>4</b>) are developed. The first approach includes a reaction between chlorohydrin <b>7</b> and NaH in THF. The second involves the formation of epoxide in the reaction of corresponding diacetate <b>6</b> with sodium <i>tert</i>-butoxide. One possible mechanism of this reaction is proposed to explain unexpected outcomes in the regio- and stereospecificity of epoxide (1<i>S</i>,5<i>S</i>,6<i>R</i>)<i>-</i><b>4</b> formation. The epoxide ring in (1<i>S</i>,5<i>S</i>,6<i>R</i>)<i>-</i><b>4</b> is then opened by various <i>S</i>- and <i>O</i>-nucleophiles. This series of reactions allows for the stereoselective synthesis of diverse derivatives of the monoterpenoid Prottremine <b>1</b>, a compound known for its antiparkinsonian activity, including promising antiparkinsonian properties.https://www.mdpi.com/1420-3049/28/21/7303monoterpenenucleophilic substitutionsynthetic methodsProttremineepoxide |
| spellingShingle | Alexandra V. Podturkina Oleg V. Ardashov Konstantin P. Volcho Nariman F. Salakhutdinov A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in <i>para</i>-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents Molecules monoterpene nucleophilic substitution synthetic methods Prottremine epoxide |
| title | A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in <i>para</i>-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents |
| title_full | A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in <i>para</i>-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents |
| title_fullStr | A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in <i>para</i>-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents |
| title_full_unstemmed | A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in <i>para</i>-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents |
| title_short | A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in <i>para</i>-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents |
| title_sort | new stereoselective approach to the substitution of allyl hydroxy group in i para i mentha 1 2 diol in the search for new antiparkinsonian agents |
| topic | monoterpene nucleophilic substitution synthetic methods Prottremine epoxide |
| url | https://www.mdpi.com/1420-3049/28/21/7303 |
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