Synthesis of Azaphilones and Related Molecules by Employing Cycloisomerization of o-Alkynylbenzaldehydes

Right to the core: Gold(III)‐catalyzed cycloisomerization of o‐alkynylbenzaldehydes to 2‐benzopyrylium salts and subsequent in situ oxidation have been employed to prepare the core structure of azaphilone natural products, such as the sphingosine kinase inhibitor S‐15183 (see scheme, DCE=1,2‐dichlor...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2004-02, Vol.43 (10), p.1239-1243
Main Authors: Zhu, Jianglong, Germain, Andrew R., Porco Jr, John A.
Format: Article
Language:English
Subjects:
alkynes
azaphilones
cycloisomerization
gold
Lewis acid catalysis
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Summary:Right to the core: Gold(III)‐catalyzed cycloisomerization of o‐alkynylbenzaldehydes to 2‐benzopyrylium salts and subsequent in situ oxidation have been employed to prepare the core structure of azaphilone natural products, such as the sphingosine kinase inhibitor S‐15183 (see scheme, DCE=1,2‐dichloroethane, TFA=trifluoroacetic acid)), and several unnatural azaphilones.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353037