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D-Homo Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr188

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. D-Homo Rearrangement. Comprehensive Organic Name Reactions and Reagents. 188:877–880.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

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.

Keywords:

  • 17β-hydroxy-20-ketosteroid;
  • Lewis acids;
  • 17aα-hydroxy-D-homo derivatives;
  • diazotization