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

Aryeh A. Frimer, Shlomo Ripstos, Vered Marks, Gladis Aljadeff, Judith Hameiri-Buch, Pessia Gilinsky-Sharon

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)8361-8372
Number of pages12
JournalTetrahedron
Volume47
Issue number39
DOIs
StatePublished - 23 Sep 1991

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