A new electrochemical system for stereoselective allylic hydroxylation of cholesteryl acetate with dioxygen induced by iron picolinate complexes.
The oxygenation reaction of cholesteryl acetate 1 was examined with the Fe(III)(PA)(3)/O(2)/MeCN system using an electrochemical method. The constant potential technique gave mainly the 7-hydroxylated product stereoselectively, along with the 7-oxo product. This oxygenation system is mechanistically unique, requiring iron catalyst, dioxygen, and both cathode and anode.
Okamoto
Iwao
I
Showa Pharmaceutical University, 3-165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan.
Funaki
Wataru
W
Nakaya
Kyosuke
K
Kotani
Eiichi
E
Takeya
Tetsuya
T
D000498:Allyl Compounds / Q000737:chemistry* / Q000378:metabolism; D002788:Cholesterol Esters / Q000737:chemistry* / Q000378:metabolism; D004563:Electrochemistry; D006900:Hydroxylation; D007501:Iron / Q000737:chemistry* / Q000378:metabolism; D010100:Oxygen / Q000737:chemistry* / Q000378:metabolism; D010848:Picolinic Acids / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
D000498:Allyl Compounds; D002788:Cholesterol Esters; D010848:Picolinic Acids; D007501:Iron; C060123:cholesterol acetate; C030614:picolinic acid; D010100:Oxygen