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

被引：35

作者：

Iida, Takashi ^{[1
]}

Ogawa, Shoujiro

Hosoi, Keiji

Makino, Mitsuko

Fujimoto, Yasuo

Goto, Takaaki

Mano, Nariyasu

Goto, Junichi

Hofmann, Alan F.

机构：

[1] Nihon Univ, Coll Humanities & Sci, Dept Chem & Gen Studies, Setagaya Ku, Tokyo 1568550, Japan

[2] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

[3] Tohoku Univ Hosp, Dept Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808574, Japan

[4] Univ Calif San Diego, Dept Med, La Jolla, CA 92093 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 03期

关键词：

D O I：

10.1021/jo061800g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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, 5 beta-cholane, or 5 alpha-cholestane structure, regioselective oxyfunctionalization and/or oxidative degradation occurred to give a variety of novel and uncommon derivatives in one step.

引用

页码：823 / 830

页数：8

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