PMID: 11674459Oct 25, 2001Paper

Improved Syntheses and Some Selective Transformations of 2,2,4,4-Tetrachloro-8-oxabicyclo[3.2.1]oct-6-en-3-ones

The Journal of Organic Chemistry
Stefan SendelbachBaldur Föhlisch

Abstract

The methyl- and alkenyl-substituted furans 1b-h react with pentachloroacetone (2) and sodium 2,2,2-trifluoroethoxide solution to form the title compounds 3b-h in good yield. With the furans 1i-m bearing an oxygen or a sulfur heteroatom in the side chain, moderate yields are obtained. Dechlorination of the [4+3] cycloadducts 3 with the Zn-Cu couple leads to the corresponding oxabicyclic ketones 4. On catalytic hydrogenation of the tetrachlorooxabicyclooctenones 3a-c hydrogenolysis of the exo-carbon-chlorine bonds occurs, leading to the endo-2,endo-4-dichloro-8-oxabicyclooctan-3-ones 8a-c. With lithium aluminum hydride and Grignard reagents, 8a and 3a form the endo-3-alcohols 12a-c and 13, respectively, the latter with uncertain configuration at C-3, in a highly stereoselective manner. The ether bridge in the dechlorinated oxabicyclooctenones 4b, 4f, and 4g can be cleaved by means of trimethylsilyl triflate/triethylamine to produce the tropones 5b, 5f, and 5g. Hydrogenation of 1,5-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (4c), followed by Wolff-Kishner reduction, affords 1,5-dimethyl-8-oxabicyclo[3.2.1]octane (7). m-Chloroperbenzoic acid epoxidizes the alkenyl side chain of the tetrachlorinated oxabicycles 3d, 3e, 3g, and 3h in...Continue Reading

References

Jan 1, 1992·Archiv der Pharmazie·F Eiden, A Kainz
Dec 1, 1964·Tetrahedron·M A GianturcoV Flanagan
Aug 1, 1966·The Journal of Organic Chemistry·H O HouseC D Slater

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Citations

Nov 11, 2010·Chemical Communications : Chem Comm·Michael Harmata
Nov 17, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Baldur Föhlisch, Stefan Reiner
Nov 6, 2018·Chemical Society Reviews·Zengsheng YinPauline Chiu
Oct 9, 2007·Chemistry : a European Journal·M Carmen CarreñoM Jesús Sanz-Cuesta
Aug 28, 2018·European Journal of Organic Chemistry·Samantha M GibsonTom D Sheppard
Oct 12, 2010·Organic Letters·Fangmiao YuHongbin Zhai
Sep 27, 2003·The Journal of Organic Chemistry·Richard S GraingerJonathan W Steed
Jun 8, 2001·Journal of the American Chemical Society·K Lee, J K Cha
Jul 18, 2001·Journal of the American Chemical Society·J C Lee, J K Cha

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