ORGN 125 |
| Jorge A. R. Salvador1, Samuel M. Silvestre1, and James H. Clark2. (1) Laboratório de Química Farmacêutica, Faculdade de Farmácia da Universidade de Coimbra, Rua do Norte, 3000-295 Coimbra, Portugal, (2) Centre For Clean Technology, Department of Chemistry, University of York, Heslington, YO10 5DD York, United Kingdom |
The synthesis of 5β,6β-epoxides is a useful reaction since this group is present in many biologically active steroids. Chandrasekaran et al. and more recently a number of other groups including ourselves, demonstrated that these epoxides can be obtained from D5-steroids using biphasic systems involving potassium permanganate and metal salts. Recently the β-epoxidation of D5-steroids using ketones as catalysts and oxone as the terminal oxidant was reported. The use of molecular oxygen or air as the oxidant in the presence of either metalloporphyrin or Mn(II), Ni(II), Fe(III) and Co(II) complexes as catalysts is of greater industrial interest, but a difficult separation step is needed to remove the catalyst which cannot easily be reused. Here we report the use of some heterogeneous cobalt catalysts for the 5β,6β-epoxidation of D5-steroids under Mukaiyama reaction conditions (Scheme 1). |
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |