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

Franco Bellesia,Chiara Danieli,Laurent De Buyck,Roberta Galeazzi,Franco Ghelfi,Adele Mucci,Mario Orena,Ugo M Pagnoni,Andrew F Parsons,Fabrizio Roncaglia

doi:10.1016/j.tet.2005.09.140

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

Franco Bellesia, Chiara Danieli + Show 8 more

https://doi.org/10.1016/j.tet.2005.09.140

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Journal: Tetrahedron	Publication Date: Nov 7, 2005
Citations: 32

Affiliation: University of Modena and Reggio Emilia, Marche Polytechnic University, Ghent University, University of York

#Atom Transfer Radical Cyclisation #Chaetomellic Anhydride + Show 4 more

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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.

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