Industrial Synthesis of 4-Chloro,11β-arylestradiol: How to Circumvent a Poor Diastereoselectivity

An industrial synthesis of 11β-arylestrone derivatives is described, based on the conjugate opening of a mixture of allylic 5(10)-α and -β epoxides by an aryl cuprate generated catalytically, followed by hydrolysis and subsequent aromatisation of the isomeric mixture of arylation products. An origin...

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Bibliographic Details
Published in:Organic process research & development 2004-03, Vol.8 (2), p.219-228
Main Authors: Prat, Denis, Benedetti, Françoise, Franc Girard, Gilles, Nait Bouda, Lahlou, Larkin, John, Wehrey, Christian, Lenay, Jacques
Format: Article
Language:English
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Summary:An industrial synthesis of 11β-arylestrone derivatives is described, based on the conjugate opening of a mixture of allylic 5(10)-α and -β epoxides by an aryl cuprate generated catalytically, followed by hydrolysis and subsequent aromatisation of the isomeric mixture of arylation products. An original method for selective 4-chlorination of estrone derivatives is also described.
ISSN:1083-6160
1520-586X
DOI:10.1021/op0341622