231606-24-9Relevant articles and documents
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
Bellesia, Franco,Danieli, Chiara,Buyck, Laurent De,Galeazzi, Roberta,Ghelfi, Franco,Mucci, Adele,Orena, Mario,Pagnoni, Ugo M.,Parsons, Andrew F.,Roncaglia, Fabrizio
, p. 746 - 757 (2006)
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.