Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450: Osmiumporphyrin complex/tert-butyl hydroperoxide system

Takashi Iida, Shoujiro Ogawa, Keiji Hosoi, Mitsuko Makino, Yasuo Fujimoto, Takaaki Goto, Nariyasu Mano, Junichi Goto, Alan F. Hofmann

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

(Chemical Equation Presented) tert-Butyl hydroperoxide catalyzed by (5,10,15,20-tetramesitylporphyrinate) osmium(II) carbonyl [Os(TMP)CO] complex was found to be a highly efficient versatile oxidant for C-H carbons in steroid substrates. When reacted with representative steroids with an estrane, pregnane, 5β-cholane, or 5α-cholestane structure, regioselective oxyfunctionalization and/or oxidative degradation occurred to give a variety of novel and uncommon derivatives in one step.

Original languageEnglish
Pages (from-to)823-830
Number of pages8
JournalJournal of Organic Chemistry
Volume72
Issue number3
DOIs
Publication statusPublished - 2007 Feb 2

ASJC Scopus subject areas

  • Organic Chemistry

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