Synthesis of 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one, a D-ring precursor of 9,11-secosterols

Autor:	Marek Kõllo, Kristi Rõuk, Margus Lopp
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	asymmetric oxidation of sulfide titanium-catalytic oxidation enantiomeric sulfoxide 11-secosterols. Science
Zdroj:	Proceedings of the Estonian Academy of Sciences, Vol 71, Iss 4, Pp 307-313 (2022)
Druh dokumentu:	article
ISSN:	1736-6046 1736-7530
DOI:	10.3176/proc.2022.4.01
Popis:	The asymmetric oxidation of a key intermediate for 9,11-secosterol synthesis, 2-[(4-methylphenyl)thio]-2-cyclopenten-1-one 2 with a Ti(iPrO)4/(+)-DET/TBHP complex was studied. The kinetic resolution of racemic 2-[(4-methylphenyl)sulfinyl]- 2-cyclopenten-1-one 1 by oxidation with the same Ti-complex was also carried out. In both cases enantioenriched 2-(S)-[(4-methylphenyl)sulfinyl]-2-cyclopenten-1-one 1 was obtained in satisfactory yields and sufficient enantiomeric purity for further enantioenrichment by recrystallization. The obtained results afford simple access to the D-ring precursor of 9,11-secosterols.
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/5fee0f27056a41899279290313f9429b Zobrazit plný text záznamu View record in DOAJ Plný text ve formátu PDF