Au(I)-catalyzed synthesis of 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization.

Research paper by Jaya Kishore JK Vandavasi, Wan-Ping WP Hu, Siva Senthil Kumar SS Boominathan, Bing-Chun BC Guo, Cheng-Tien CT Hsiao, Jeh-Jeng JJ Wang

Indexed on: 07 Jul '15Published on: 07 Jul '15Published in: Chemical Communications

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Abstract

A sustainable and simple Au(I) catalytic system to synthesise 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization is described. The key advantages of this reaction are selectivity, good functional group tolerance and a new approach for synthesis of oxabicyclic and oxatricyclic systems.

Au(I)-catalyzed synthesis of 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization.

Abstract

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Au(I)-catalyzed synthesis of 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization.

Abstract

More like this:

Locked nucleosides based on oxabicyclo[3.2.1]octane and oxabicyclo[2.2.1]heptane skeletons.

Synthesis of 7-oxabicyclo[2.2.1]heptanes and 8-oxabicyclo[3.2.1]octanes from C-glycosides via an intramolecular cyclization.

Molecular mechanism underlying antileishmanial effect of oxabicyclo[3.3.1]nonanones: inhibition of key redox enzymes of the pathogen.

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