Chemical and Pharmaceutical Bulletin p. 64 - 70 (1999)
Update date:2022-08-03
Topics:
Takeya, Tetsuya
Egawa, Hirotaka
Inoue, Natsu
Miyamoto, Akiko
Chuma, Toichiro
Kotani, Eiichi
The reaction of cholesteryl acetate 1 with a Fe(III)(PA; picolinate)3/H2O2/MeCN system (reagent system A), a simple model system for mono-oxygenases, gave mainly the 7α-hydroxylation product 2a, along with 7-ketonization product 3 and the 5,6-epoxidation product 4. On the other hand, reaction of 1 using a Fe(PA)3/peracetic acid (AcOOH)/MeCN system (reagent system c) or a Fe(III)(ClO4)3 · 9H2O-picolinic acid(PAH)- pyridine(Py)/AcOOH/MeCN system (reagent system F), provided 4 predominantly without formation of 2a. The former reaction may proceed via the dimeric Fe(III)-Fe(V) manifold complex, (PAH)(PA)2Fe(III)-O-O-Fe(V)=O(PA)2 (VII) as a hypothetically active species and a nonradical pathway, and the latter may proceed through monomeric iron complexes, [(PAH)(PA)2Fe(V)=O]+ (IX) and [(PAH)(PA)2Fe(V)(OH)(OOH)I+ (X).
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