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

doi:10.1021/jo061800g

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

University Hospital (not affiliated with any section)

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	823-830
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	72
Issue number	3
DOIs	https://doi.org/10.1021/jo061800g
Publication status	Published - 2007 Feb 2

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo061800g

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Iida, T., Ogawa, S., Hosoi, K., Makino, M., Fujimoto, Y., Goto, T., Mano, N., Goto, J., & Hofmann, A. F. (2007). Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450: Osmiumporphyrin complex/tert-butyl hydroperoxide system. Journal of Organic Chemistry, 72(3), 823-830. https://doi.org/10.1021/jo061800g

Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450 : Osmiumporphyrin complex/tert-butyl hydroperoxide system. / Iida, Takashi; Ogawa, Shoujiro; Hosoi, Keiji; Makino, Mitsuko; Fujimoto, Yasuo; Goto, Takaaki ; Mano, Nariyasu; Goto, Junichi; Hofmann, Alan F.

In: Journal of Organic Chemistry, Vol. 72, No. 3, 02.02.2007, p. 823-830.

Research output: Contribution to journal › Article

Iida, Takashi ; Ogawa, Shoujiro ; Hosoi, Keiji ; Makino, Mitsuko ; Fujimoto, Yasuo ; Goto, Takaaki ; Mano, Nariyasu ; Goto, Junichi ; Hofmann, Alan F. / Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450 : Osmiumporphyrin complex/tert-butyl hydroperoxide system. In: Journal of Organic Chemistry. 2007 ; Vol. 72, No. 3. pp. 823-830.

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