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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Published inAngewandte Chemie (International ed.) Vol. 43; no. 10; pp. 1239 - 1243
Main Authors Zhu, Jianglong, Germain, Andrew R., Porco Jr, John A.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.02.2004
WILEY‐VCH Verlag
Wiley
Subjects
alkynes
azaphilones
Chemistry
Chemistry, Multidisciplinary
cycloisomerization
gold
Lewis acid catalysis
Physical Sciences
Science & Technology
FUNGI
azaphilones
alkynes
EFFICIENT SYNTHESIS
IODOXYBENZOIC ACID
CATALYST
Lewis acid catalysis
gold
KETONES
4+2 CYCLOADDITION
SONOGASHIRA COUPLING REACTIONS
cycloisomerization
DERIVATIVES
CYCLIZATION
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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.
Bibliography:ArticleID:ANIE200353037
ark:/67375/WNG-0Q4DG8JL-J
We thank Dr. Takafumi Kohama (Sankyo Co. LTD.) for providing 1H and 13C NMR spectra of S-15183a and Dr. Emil Lobkovsky (Cornell University) for X-ray crystal structure analysis. We thank CEM Corporation (Matthews, NC) for providing the Explorer microwave system, Bristol-Myers Squibb for an unrestricted Grant in Synthetic Organic Chemistry (J.A.P, Jr.), and Novartis Pharma AG for research support.
istex:A218FEDE5468EDEABC8E63F5E4077F0122C60EC0
1
H and
13
C NMR spectra of S‐15183a and Dr. Emil Lobkovsky (Cornell University) for X‐ray crystal structure analysis. We thank CEM Corporation (Matthews, NC) for providing the Explorer microwave system, Bristol‐Myers Squibb for an unrestricted Grant in Synthetic Organic Chemistry (J.A.P, Jr.), and Novartis Pharma AG for research support.
We thank Dr. Takafumi Kohama (Sankyo Co. LTD.) for providing
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353037