The photosensitized oxidation of α-keto enols: A singlet oxygen approach to 2-oxasteroids

Autor:	Pessia Gilinsky-Sharon, Judith Hameiri-Buch, Aryeh A. Frimer, Vered Marks, Gladis Aljadeff, Shlomo Ripstos
Rok vydání:	1991
Předmět:	chemistry.chemical_classification Chemistry Singlet oxygen Organic Chemistry Photochemistry Biochemistry Medicinal chemistry Catalysis chemistry.chemical_compound Cyclohexenone Drug Discovery Hemiacetal Photosensitizer Singlet state Fluoride Lactone
Zdroj:	Tetrahedron. 47:8361-8372
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)96177-0
Popis:	Fluoride ion catalyzed photosensitized singlet oxygenation of 2-hydroxycyclohexa-2,5-dien-1-ones 15a and b and the related steroidal α-keto enols 18a–g, generated the cyclohexenone lactols 16a–b and the corresponding steroidal analogs 19a–g generally in moderate to good yields (60–75%). Since the lactols can be conveniently reduced to the desired 2-oxasteroids in high yields, this 1O2 route presents itself as a synthetically acceptable alternative to the previously reported BCA approach for the preparation of 2-oxasteroids, especially in the case of base sensitive compounds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9289361d5dc58a32bb9917165117a385 https://doi.org/10.1016/s0040-4020(01)96177-0 Zobrazit plný text záznamu