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

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Abstract

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.