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Molecular complexity from aromatics. Cycloaddition of cyclohexa-2,4-dienones, sigmatropic 1,2-acyl shift and ring-closing metathesis: a new, efficient, and stereoselective synthesis of (±)-hirsutic acid C and medium ring carbocycles
Authors:Vishwakarma Singh  Shantanu Pal  Shaikh M Mobin
Institution:a Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India
b National Single Crystal X-ray Diffraction Facility, Indian Institute of Technology Bombay, Mumbai 400 076, India
Abstract:A new, stereoselective formal synthesis of hirsutic acid and medium ring carbocyclic systems from salicyl alcohol is described. Cycloaddition between electron deficient partners such as cyclohexa-2,4-dienone and methylmethacrylate, triplet sensitized 1,2-acyl shift and ring-closing metathesis are the key features of our approach.
Keywords:Cyclohexa-2  4-dienone  Diels-Alder reaction  Oxa-di-π-methane rearrangement  Hirsutic acid
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