The applicability of sulfoxide Michael acceptor--2-sulfinyl]-2-cyclopenten-1-one in constructing the carbon skeleton of 9,11-secosterols

A possibility of use of the Michael addition reaction of the A,B-ring fragment enolate to sulfoxide 2-(S)-[(4-methyl-phenyl)sulfmyl]-2-cyclopenten-1-one for constructing the main skeleton of 9,11-secosterols was studied. The reaction was conducted with the racemic or the enantiomerically enriched su...

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Bibliographic Details
Published in:Proceedings of the Estonian Academy of Sciences 2024-09, Vol.73 (3), p.223
Main Authors: Rouk, Kristi, Kollo, Marek, Jarving, Ivar, Lopp, Margus
Format: Article
Language:English
Subjects:
Chemical research
Electron donor-acceptor complexes
Oxides
Sulfur compounds
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Summary:A possibility of use of the Michael addition reaction of the A,B-ring fragment enolate to sulfoxide 2-(S)-[(4-methyl-phenyl)sulfmyl]-2-cyclopenten-1-one for constructing the main skeleton of 9,11-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. Keywords: Michael addition, sulfoxides, 9,11-secosterols.
ISSN:1736-6046
DOI:10.3176/proc.2024.3.06