Improved synthesis of a protected 11-oxoestrone

An improved synthesis of 11-oxoestrone-3-acetate-17-ethyleneketal is reported. Adjustments are proposed for the oxidation of estrone by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone into 9(11)-dehydroestrone. A complete hydroboration-oxidation of the resulting ketal, by means of borane-methylsulfide com...

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Bibliographic Details
Published in:Steroids 1995-12, Vol.60 (12), p.809-811
Main Authors: Stéphan, Elie, Zen, Régine, Authier, Laurent, Jaouen, Gérard
Format: Article
Language:English
Subjects:
3-acetoxy-17-ethylenedioxyestra-1,3,5-trien-11-one
Acetylation
Alicyclic compounds, terpenoids, prostaglandins, steroids
Aluminum Oxide - chemistry
Chemistry
Chromates - chemistry
dehydrogenation of estrone
Estrone - analogs & derivatives
Estrone - chemical synthesis
Estrone - chemistry
Exact sciences and technology
hydroboration of dehydroestrone-17-ethyleneketal
Magnetic Resonance Spectroscopy
Organic chemistry
Oxidation-Reduction
Preparations and properties
Pyridinium Compounds - chemistry
Spiro Compounds - chemical synthesis
Steroids
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Summary:An improved synthesis of 11-oxoestrone-3-acetate-17-ethyleneketal is reported. Adjustments are proposed for the oxidation of estrone by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone into 9(11)-dehydroestrone. A complete hydroboration-oxidation of the resulting ketal, by means of borane-methylsulfide complex, gives the corresponding 11-hydroxy derivative. This latter compound is then acetylated for successful oxidation with pyridinium chlorochromate on alumina. The overall yield is 30%.
ISSN:0039-128X
1878-5867
DOI:10.1016/0039-128X(95)00145-G