Document Detail

An improved synthesis of 18-norandrost-4-ene-3,17-dione.
MedLine Citation:
PMID:  8475519     Owner:  NLM     Status:  MEDLINE    
We describe the synthesis of 13 beta- and 13 alpha-H-18-nor-androst-4-ene-3,17-dione (1a and 1b) from 18-hydroxyprogesterone (18-->20) hemiketal, via the 18-acetoxy-17 beta-hydroxyandrost-4-en-3-one formed by a modified Baeyer-Villiger reaction. Saponification of 18-acetoxyandrost-4-ene-3,17-dione with sonication, then retroaldolization in the presence of a formaldehyde trap, methone, afforded the mixture of 1a and 1b with 80% yield in a "one-pot" procedure and at room temperature. This yield was greatly improved, compared with the already published procedure.
E Davioud; P Schambel; A Viger; A Marquet
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Steroids     Volume:  58     ISSN:  0039-128X     ISO Abbreviation:  Steroids     Publication Date:  1993 Mar 
Date Detail:
Created Date:  1993-05-17     Completed Date:  1993-05-17     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0404536     Medline TA:  Steroids     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  141-4     Citation Subset:  IM    
Laboratoire de Chimie Organique Biologique, URA CNRS 493, Université Pierre et Marie Curie, Paris, France.
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MeSH Terms
Hydrogen Peroxide
Hydroxyprogesterones / chemistry*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Norandrostanes / chemical synthesis*
Reg. No./Substance:
0/Hydroxyprogesterones; 0/Norandrostanes; 596-69-0/18-hydroxyprogesterone; 7722-84-1/Hydrogen Peroxide; 93998-22-2/18-norandrost-4-ene-3,17-dione

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