Journal
TETRAHEDRON
Volume 67, Issue 13, Pages 2434-2440Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.01.083
Keywords
Steroid; Chemical synthesis; Furanic derivative; Ring-closing metathesis
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Funding
- Canadian Institutes of Health Research (CIHR)
- Canadian Breast Cancer Research Alliance (CBCRA)
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The stereoselective synthesis of furanic-steroid derivatives involving ring-closing metathesis and catalytic hydrogenation as key steps is described. The synthetic strategy was first illustrated by the synthesis of the furanic-estrane derivative 1 in seven steps starting from estrone and 2-methylene-propane-1,3-diol. This compound initially targeted as a potential inhibitor of 17 beta-hydroxysteroid dehydrogenase type 1 by a docking experiment was found to inhibit the enzyme. The scope of this new strategy was also extended to furanic-androstane derivatives by synthesizing compound 20. (C) 2011 Elsevier Ltd. All rights reserved.
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