Synthesis of (±)-3-Methoxyestra-1,3,5(10)-trienes by the Repetitive Use of Negishi Reagent

The repetitive use of Cp2ZrBu2 (Negishi reagent) was applied in the synthesis of three 3-methoxyestra-1,3,5(10)-trienone isomers within four steps from the advanced intermediate 11. The overall synthesis is based on three zirconium-mediated reactions:  (a) oxidative addition of a benzyl ether, (b) c...

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Bibliographic Details
Published in:Organic letters 2006-03, Vol.8 (7), p.1315-1318
Main Authors: Herrmann, Pavel, Kotora, Martin, Buděšínský, Miloš, Šaman, David, Císařová, Ivana
Format: Article
Language:English
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Summary:The repetitive use of Cp2ZrBu2 (Negishi reagent) was applied in the synthesis of three 3-methoxyestra-1,3,5(10)-trienone isomers within four steps from the advanced intermediate 11. The overall synthesis is based on three zirconium-mediated reactions:  (a) oxidative addition of a benzyl ether, (b) cyclization of an allyl-ene compound, and (c) cyclocarbonylation of a diene. The presented synthesis demonstrates that complex organic compounds can be prepared by the repetitive use of one reagent.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol053119r