Synthesis of Azaphilones and Related Molecules by Employing Cycloisomerization of o‐Alkynylbenzaldehydes
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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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z53037_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.Keywords:
Cycloisomerization
Trifluoroacetic acid
Abstract Gold(I)‐catalyzed cycloisomerization of ortho ‐(propargyloxy)arenemethylenecyclopropanes afforded two different types of products, that is, products of methylenecyclopropane migration and cycloisomerization products of the methylenecyclopropane moiety, controlled jointly by electronic and steric effects of the adjacent substituents. Furthermore, the corresponding cycloisomerization products could be also produced in an enantiomerically enriched manner.
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A gold-catalysed cycloisomerization of 1,5-diynes is described, which offers a selective approach to access 1,3,4-trisubstituted pyrroles.
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Gold-catalyzed cycloisomerization of 1,5-enynes has been investigated with the aid of density functional theory calculations at the B3LYP level of theory. We have examined how substituents influence the reaction paths in the cycloisomerization of 1,5-enynes catalyzed by both AuCl and [AuL]+ (L = phosphine).
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An efficient synthetic method to prepare architecturally challenging spiro tetrahydro‐3 H ‐dicyclopenta[ a,b ]naphthalene derivatives from Au(I)‐catalyzed intramolecular sequential cycloisomerization of linear 1,3,9‐ene‐allene‐ynes is described. The proposed cycloisomerization pathway involves an initial gold‐catalyzed 1,3‐ene‐allene cycloisomerization, followed by a formal [4+2] cycloaddition to give fused spirocarbocyclic products containing a quaternary centre.
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This chapter contains sections titled: Introduction Cycloisomerization of CO onto CCC Cycloisomerization of CO onto CC Cycloisomerization of CN onto CCC Cycloisomerization of CN onto CC Ene–Yne Cycloisomerization: CC onto CC Other Transformations Conclusion References
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Abstract A simple and highly efficient method for the preparation of tetrasubstituted furans starting from readily accessible propargylic alcohols and commercially available 1,3‐dicarbonyl compounds has been developed. The process, which proceeds in a one‐pot manner, involves the initial propargylation of the 1,3‐dicarbonyl compound promoted by trifluoroacetic acid, and subsequent cycloisomerization of the resulting γ‐ketoalkyne catalyzed by the 16‐electron allyl‐ruthenium( II ) complex [Ru(η 3 ‐2‐C 3 H 4 Me)(CO)(dppf)][SbF 6 ].
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