TY - JOUR
T1 - The photosensitized oxidation of α-keto enols
T2 - A singlet oxygen approach to 2-oxasteroids
AU - Frimer, Aryeh A.
AU - Ripstos, Shlomo
AU - Marks, Vered
AU - Aljadeff, Gladis
AU - Hameiri-Buch, Judith
AU - Gilinsky-Sharon, Pessia
PY - 1991/9/23
Y1 - 1991/9/23
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0025946488&partnerID=8YFLogxK
U2 - 10.1016/s0040-4020(01)96177-0
DO - 10.1016/s0040-4020(01)96177-0
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
AN - SCOPUS:0025946488
SN - 0040-4020
VL - 47
SP - 8361
EP - 8372
JO - Tetrahedron
JF - Tetrahedron
IS - 39
ER -