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A Synthetic Approach to Antiprogestational Steroids

Ayerman, Farah (1996). A Synthetic Approach to Antiprogestational Steroids. (Unpublished Doctoral thesis, City, University of London)

Abstract

The nature and uses of some steroidal hormones and anti-hormones are reviewed, with an emphasis on the anti-progestins which have anti-implantation activity. A new type of steroid structure has been designed which combines two types of structural elements, namely an A-nor skeleton and an 11-aryl substituent, which are separately known to display anti-implantation properties.

It is demonstrated that a thallium-mediated ring contraction of steroidal 4-en-3-ones carrying an 11-keto group provides entry to a functionalised A-nor steroid skeleton which can then be arylated using organolithium reagents. Manipulation of the functionalities led to the successful synthesis of ll-phenyl-A-nor-5ft-androst-2,17- dione, which should be a valuable intermediate for the generation of a set of 11-arylated A-nor steroids for biological evaluation.

Publication Type: Thesis (Doctoral)
Subjects: Q Science > QD Chemistry
Departments: Doctoral Theses
Doctoral Theses > School of Health Sciences
School of Health Sciences
URI: http://openaccess.city.ac.uk/id/eprint/20855
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