Semi-synthesis of a novel hybrid isoxazolidino withaferin via chemoselective and diastereoselective 1,3-dipolar nitrone cycloaddition reaction |
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Authors: | Ramkrishna Mandal Meenakshi Singh Amrutha A.V. Krishnan Yogita H. Dahat V. Ravichandiran |
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Affiliation: | National Institute of Pharmaceutical Education and Research (NIPER), Kolkata, India |
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Abstract: | AbstractA facile, atom-economic synthesis of isoxazilidino withaferin, a novel hybrid of withaferin A, has been accomplished via two-step reaction of nitrone synthesis followed by nitrone 1,3-dipolar cycloaddition. The reaction is highly chemoselective (preferential reaction only on one of the two double bonds present on withaferin A) and diastereoselective affording exclusively the cis-fused products. The structure was determined by detailed analysis of 1D, 2D NMR and mass spectral data. |
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Keywords: | Withaferin A nitrone-cycloaddition semi-synthesis isoxazolidine 2D NMR (HSQC HMBC COSY NOESY) |
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