Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. D-Homo Rearrangement. Comprehensive Organic Name Reactions and Reagents. 877–880.
- Published Online: 15 SEP 2010
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The D-homo rearrangement occurs at the D-ring of steroids without the loss of carbon. In this rearrangement, when 17-hydroxy-20-ketosteroids are treated with either bases or acids (Lewis acids), they will rearrange and give six-membered D-rings; the products resulting from the base treatment differ greatly from those caused by the acid treatment, showing characteristic stereospecificity. This rearrangement has been also reported to occur when a carbocation forms at position 20 without a carbonyl group. This rearrangement has wide application for the preparation of a series of steroid derivatives.
- Lewis acids;
- 17aα-hydroxy-D-homo derivatives;