A new route to (±)-erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH3ONa/CH3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one |
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Authors: | Laurent De Buyck Franco Ghelfi Ugo M. Pagnoni Mariella Pattarozzi Fabrizio Roncaglia |
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Affiliation: | a Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, University of Gent, Coupure Links 653, B-9000 Gent, Belgium b Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, via Campi 183, 41100 Modena, Italy c Department of Chemistry, University of York, Heslington, York YO10 5DD, UK |
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Abstract: | The rearrangement of a trichloro-pyrrolidin-2-one, prepared by the CuCl-TMEDA catalyzed atom transfer radical cyclization of N-alkyl-N-(3-chloro-2-propenyl)-2,2-dichloromyristamide, with n-propylamine or CH3ONa/CH3OH, is the key step of a new, short and inexpensive route to chaetomellic anhydride C and (±)-erythro-roccellic acid. |
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Keywords: | Radicals Cyclizations Pyrrolidinones Rearrangements |
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