Cross metathesis approach to retinoids and other β-apocarotenoids

Autor:	Jadwiga Maj, Agnieszka Dzieszkowska, Agnieszka Wojtkielewicz, Jacek W. Morzycki
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Double bond Organic Chemistry Regioselectivity Retinyl acetate Cleavage (embryo) Metathesis Biochemistry Catalysis chemistry.chemical_compound chemistry Drug Discovery Salt metathesis reaction Organic chemistry Canthaxanthin
Zdroj:	Tetrahedron. 67:6868-6875
ISSN:	0040-4020
Popis:	Cross metathesis (CM) reactions between polyenes, such as β-carotene, canthaxanthin or retinyl acetate, and various alkenes or dienes in the presence of second generation Hoveyda–Grubbs (H II) or Grubbs (G II) catalysts were investigated. Depending on the cross partner different apocarotenoids were obtained. Cross metathesis reactions of retinyl acetate proved to be fully regioselective. Carotenoid CM reactions afforded mixtures of two products due to competing cleavage of the C11–C12 and C15–C15′ double bonds. However, regioselectivity can be controlled by choice of appropriate reaction conditions. The reactions of polyenes with dienes worked better in respect of yields and diastereoselectivities than those with monounsaturated cross partners.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e61b3f0f4b4fe7915781ba189a519a9d https://doi.org/10.1016/j.tet.2011.06.086 Zobrazit plný text záznamu Full Text from ScienceDirect