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 |
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Authors: | Vishwakarma Singh Shantanu Pal Shaikh M Mobin |
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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 |
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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. |
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Keywords: | Cyclohexa-2 4-dienone Diels-Alder reaction Oxa-di-π-methane rearrangement Hirsutic acid |
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