Semi-synthesis of a novel hybrid isoxazolidino withaferin via chemoselective and diastereoselective 1,3-dipolar nitrone cycloaddition reaction

A 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 bo...

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Bibliographic Details
Published in:	Natural product research Vol. 34; no. 15; pp. 2208 - 2218
Main Authors:	Mandal, Ramkrishna, Singh, Meenakshi, Krishnan, Amrutha A.V., Dahat, Yogita H., Bharitkar, Yogesh P., Ravichandiran, V., Hazra, Abhijit
Format:	Journal Article
Language:	English
Published:	England Taylor & Francis 02-08-2020 Taylor & Francis Ltd
Subjects:	2D NMR (HSQC Atom economy Chemical synthesis COSY Cycloaddition HMBC isoxazolidine nitrone-cycloaddition NMR NOESY Nuclear magnetic resonance semi-synthesis Semisynthesis Stereoselectivity Two dimensional analysis Withaferin A Withaferin A semi-synthesis HMBC isoxazolidine 2D NMR (HSQC NOESY nitrone-cycloaddition COSY
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Summary:	A 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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1478-6419 1478-6427
DOI:	10.1080/14786419.2019.1582045