通过细胞色素P-450模型：锇卟啉配合物/叔丁基过氧化氢体系对甾体中未活化碳进行区域选择性氧官能化

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

作者信息

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

机构信息

Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, Japan.

出版信息

J Org Chem. 2007 Feb 2;72(3):823-30. doi: 10.1021/jo061800g.

DOI:10.1021/jo061800g

PMID:17253801

Abstract

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

摘要

由羰基（5,10,15,20-四对甲苯基卟啉）锇（II）[Os(TMP)CO]配合物催化的叔丁基过氧化氢被发现是甾体底物中C-H碳的一种高效通用氧化剂。当与具有雌甾烷、孕甾烷、5β-胆甾烷或5α-胆甾烷结构的代表性甾体反应时，会发生区域选择性氧官能化和/或氧化降解，一步生成各种新颖且不常见的衍生物。