Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers
The reactions of sterols (androst-5-en-3β-ol-17-one, diosgenin, and cholesterol) and their tosylates with hydroquinone aimed at the synthesis of <i>O</i>,<i>O</i>-1,4-phenylene-linked steroid dimers were studied. The reaction course strongly depended on the conditions used. T...
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| Format: | Article |
| Language: | English |
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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/1420-3049/28/20/7068 |
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| author | Aneta M. Tomkiel Adam D. Majewski Leszek Siergiejczyk Jacek W. Morzycki |
| author_facet | Aneta M. Tomkiel Adam D. Majewski Leszek Siergiejczyk Jacek W. Morzycki |
| author_sort | Aneta M. Tomkiel |
| collection | DOAJ |
| description | The reactions of sterols (androst-5-en-3β-ol-17-one, diosgenin, and cholesterol) and their tosylates with hydroquinone aimed at the synthesis of <i>O</i>,<i>O</i>-1,4-phenylene-linked steroid dimers were studied. The reaction course strongly depended on the conditions used. The study has shown that the major reaction products are the elimination products and unusual steroid dimers resulting from the nucleophilic attack of the hydroquinone C2 carbon atom on the steroid C3 position, followed by an intramolecular addition to the C5–C6 double bond. A different reaction course was observed when montmorillonite K10 was used as a catalyst. The reaction of androst-5-en-3β-ol-17-one under the promotion of this catalyst afforded the <i>O</i>,<i>O</i>-1,4-phenylene-linked steroid dimer in addition to the disteroidal ether. The formation of the latter compound was suppressed by using 3-tosylate as a substrate instead of the free sterol. The reactions of androst-5-en-3β-ol-17-one tosylate and cholesteryl tosylate with hydroquinone catalyzed by montmorillonite K10 carried out under optimized conditions afforded the desired dimers in 31% and 67% yield, respectively. |
| first_indexed | 2024-03-10T21:00:46Z |
| format | Article |
| id | doaj.art-80a7882d1d504a62960220c735fe54e7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T21:00:46Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-80a7882d1d504a62960220c735fe54e72023-11-19T17:32:17ZengMDPI AGMolecules1420-30492023-10-012820706810.3390/molecules28207068Montmorillonite Catalyzed Synthesis of Novel Steroid DimersAneta M. Tomkiel0Adam D. Majewski1Leszek Siergiejczyk2Jacek W. Morzycki3Faculty of Chemistry, University of Bialystok, Ciołkowskiego 1K, 15-245 Bialystok, PolandFaculty of Chemistry, University of Bialystok, Ciołkowskiego 1K, 15-245 Bialystok, PolandFaculty of Chemistry, University of Bialystok, Ciołkowskiego 1K, 15-245 Bialystok, PolandFaculty of Chemistry, University of Bialystok, Ciołkowskiego 1K, 15-245 Bialystok, PolandThe reactions of sterols (androst-5-en-3β-ol-17-one, diosgenin, and cholesterol) and their tosylates with hydroquinone aimed at the synthesis of <i>O</i>,<i>O</i>-1,4-phenylene-linked steroid dimers were studied. The reaction course strongly depended on the conditions used. The study has shown that the major reaction products are the elimination products and unusual steroid dimers resulting from the nucleophilic attack of the hydroquinone C2 carbon atom on the steroid C3 position, followed by an intramolecular addition to the C5–C6 double bond. A different reaction course was observed when montmorillonite K10 was used as a catalyst. The reaction of androst-5-en-3β-ol-17-one under the promotion of this catalyst afforded the <i>O</i>,<i>O</i>-1,4-phenylene-linked steroid dimer in addition to the disteroidal ether. The formation of the latter compound was suppressed by using 3-tosylate as a substrate instead of the free sterol. The reactions of androst-5-en-3β-ol-17-one tosylate and cholesteryl tosylate with hydroquinone catalyzed by montmorillonite K10 carried out under optimized conditions afforded the desired dimers in 31% and 67% yield, respectively.https://www.mdpi.com/1420-3049/28/20/7068steroid dimers1,4-phenylene-linked dimersmontmorilloniteDHEAcholesterolsteroids |
| spellingShingle | Aneta M. Tomkiel Adam D. Majewski Leszek Siergiejczyk Jacek W. Morzycki Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers Molecules steroid dimers 1,4-phenylene-linked dimers montmorillonite DHEA cholesterol steroids |
| title | Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers |
| title_full | Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers |
| title_fullStr | Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers |
| title_full_unstemmed | Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers |
| title_short | Montmorillonite Catalyzed Synthesis of Novel Steroid Dimers |
| title_sort | montmorillonite catalyzed synthesis of novel steroid dimers |
| topic | steroid dimers 1,4-phenylene-linked dimers montmorillonite DHEA cholesterol steroids |
| url | https://www.mdpi.com/1420-3049/28/20/7068 |
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