Convenient Synthesis of Angular Triquinane from 4-Alkenylfulvene via Thermal Cycloaddition Followed by Skeletal Rearrangement of the Resulting [4 + 2] Adduct

Alkenylfulvene prepared by the annulation of allylidenetriphenylphosphorane with 1,4-ynedione proceeded thermal cycloaddition in a highly regio- and stereoselective manner to give [4 + 2] adduct which was then converted into triquinane derivative by the treatment with LHMDS-t-BuOK after hydrolysis o...

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Bibliographic Details
Published in:Chemistry letters 2008-04, Vol.37 (4), p.454-455
Main Authors: Inagaki, Sho, Imura, Keisuke, Morita, Toshio, Yoshimi, Yasuharu, Hatanaka, Minoru, Kawano, Tomikazu
Format: Article
Language:English
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Summary:Alkenylfulvene prepared by the annulation of allylidenetriphenylphosphorane with 1,4-ynedione proceeded thermal cycloaddition in a highly regio- and stereoselective manner to give [4 + 2] adduct which was then converted into triquinane derivative by the treatment with LHMDS-t-BuOK after hydrolysis of the enol ether group.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2008.454