A new electrochemical system for stereoselective allylic hydroxylation of cholesteryl acetate with dioxygen induced by iron picolinate complexes

Chem Pharm Bull (Tokyo). 2004 Jun;52(6):756-9. doi: 10.1248/cpb.52.756.

Abstract

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.

MeSH terms

  • Allyl Compounds / chemistry*
  • Allyl Compounds / metabolism
  • Cholesterol Esters / chemistry*
  • Cholesterol Esters / metabolism
  • Electrochemistry
  • Hydroxylation
  • Iron / chemistry*
  • Iron / metabolism
  • Oxygen / chemistry*
  • Oxygen / metabolism
  • Picolinic Acids / chemistry*
  • Picolinic Acids / metabolism
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Cholesterol Esters
  • Picolinic Acids
  • Iron
  • cholesterol acetate
  • picolinic acid
  • Oxygen