Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes
Jones, D. Neville and Maybury, Mark W. J. and Swallow, Steven and Tomkinson, Nicholas C. O. (1993) Novel cyclizations involving vinyl sulfones: stereoselective construction of perhydroazulenes and trans-hydrindanes. Tetrahedron Letters, 34 (52). pp. 8553-8556. ISSN 0040-4039 (https://doi.org/10.1016/S0040-4039(00)61383-7)
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Anionic species formed by treatment of vinyl sulfones with hydridoaluminates were trapped intramolecularly by esters to provide six- and seven-membered cyclic ketosulfones, e.g. I (R = Me, H, Ar = p-tolyl) and II, exemplified by the stereoselective construction of trans-hydrindanes and of perhydroazulenes. This led to formal syntheses of confertin (III) and damsinic acid.
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Item type: Article ID code: 34223 Dates: DateEvent1993PublishedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 20 Oct 2011 15:33 Last modified: 08 Apr 2024 19:29 URI: https://strathprints.strath.ac.uk/id/eprint/34223
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