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 FeIII(PA)3/O2/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 uniqu...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2004, Vol.52(6), pp.756-759
Hauptverfasser:	Okamoto, Iwao, Funaki, Wataru, Nakaya, Kyosuke, Kotani, Eiichi, Takeya, Tetsuya
Format:	Artikel
Sprache:	eng
Schlagworte:	7α-hydroxylation Allyl Compounds - chemistry Allyl Compounds - metabolism allylic hydroxylation Cholesterol Esters - chemistry Cholesterol Esters - metabolism electrochemical oxidation Electrochemistry Hydroxylation Iron - chemistry Iron - metabolism iron catalysis Oxygen - chemistry Oxygen - metabolism Picolinic Acids - chemistry Picolinic Acids - metabolism Stereoisomerism
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Beschreibung
Zusammenfassung:	The oxygenation reaction of cholesteryl acetate 1 was examined with the FeIII(PA)3/O2/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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.52.756