Zinc binding in human milk: citrate versus picolinate.
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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.
The combination of electrolysis and the Fe(III)(PA)3/O2/CH3CN system was investigated for allylic hydroxylation of octahydronaphthalene derivatives. Substrates with a bridgehead double bond gave the allylic alcohol with alpha-preference, while non-bridgehead olefin did not react smoothly. This system is a useful tool for alpha-selective allylic hydroxylation of octahydronaphthalene derivatives with a bridgehead double bond as model compounds for the AB fused ring of cholesterols.
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