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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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.

ORCID iDs

Jones, D. Neville, Maybury, Mark W. J., Swallow, Steven and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
CORE (COnnecting REpositories)