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A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate |
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| Authors: | Franco Bellesia Laurent De Buyck Franco Ghelfi Adele Mucci Ugo M. Pagnoni Fabrizio Roncaglia |
| Affiliation: | a Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, Via Campi 183, I-41100 Modena, Italy b Department of Organic Chemistry, Faculty of Biosciences Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium c Dipartimento di Scienze dei Materiali e della Terra, Università Politecnica delle Marche, Via Brecce Bianche, I-60131 Ancona, Italy d Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK |
| Abstract: | Chaetomellic anhydride A was efficiently attained in three steps, starting from 2,2-dichloropalmitic acid and 2-(3-chloro-2-propenylamino)pyridine. Atom transfer radical cyclisation selectively formed the cis-stereoisomer of the trichloropyrrolidin-2-one, which underwent a stereospecific functional rearrangement to form a substituted maleimide. The choice of 2-pyridyl, as ‘cyclisation auxiliary’ in the atom transfer radical cyclisation step, proved beneficial for hydrolysis of the maleimide to form the desired anhydride. |
| Keywords: | Halocompound Pyrrolidinone Radical reaction Rearrangement |
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