Biomimetic oxidation of unactivated carbons in steroids by a model of cytochrome P-450, oxorutheniumporphyrinate complex

Takashi Iida, Shoujiro Ogawa, Shouhei Miyata, Takaaki Goto, Nariyasu Mano, Junichi Goto, Toshio Nambara

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Biomimetic oxidation of unactivated carbons for structurally different steroids was studied with a model of cytochrome P-450, oxorutheniumporphyrinate complex, which is generated in situ by 2,6-dichloropyridine N-oxide as an oxygen donor and (5,10,15,20-tetramesitylporphyrinate) ruthenium(II) carbonyl complex and HBr as catalysts. The O-insertion positions depended significantly on specific structural features of the substrates to give novel and remote-oxygenated steroids in one step. The electrophilic oxorutheniumporphyrinate attacked predominantly allylic and benzylic β-carbons adjacent to a π-bond and/or less hindered, electron-rich tert-methine carbons in the substrates to give regio- and stereoselectively the corresponding oxo and/or hydroxy derivatives.

Original languageEnglish
Pages (from-to)873-880
Number of pages8
JournalLipids
Volume39
Issue number9
DOIs
Publication statusPublished - 2004 Sep

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Cell Biology

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