The applicability of sulfoxide Michael acceptor – 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one in constructing the carbon skeleton of 9,11-secosterols
| Autor: | Kristi Rõuk, Marek Kõllo, Ivar Järving, Margus Lopp |
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| Jazyk: | angličtina |
| Rok vydání: | 2024 |
| Předmět: | |
| Zdroj: | Proceedings of the Estonian Academy of Sciences, Vol 73, Iss 3, Pp 223-227 (2024) |
| Druh dokumentu: | article |
| ISSN: | 1736-6046 1736-7530 |
| DOI: | 10.3176/proc.2024.3.06 |
| Popis: | A possibility of use of the Michael addition reaction of the A,BÂ-ring fragment enolate to sulfoxide 2Â-(S)-Â[(4Â-methylphenyl)sulfinyl]-Â2Â-cyclopentenÂ-1Â-one for constructing the main skeleton of 9,11Â-secosterols was studied. The reaction was conducted with the racemic or the enantiomerically enriched sulfoxide as the acceptor, affording a mixture of five or three main diastereomers, respectively. It was shown that the diastereoselectivity of that addition reaction is relatively low and does not afford a competitive new route for the total synthesis of secosterols. |
| Databáze: | Directory of Open Access Journals |
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