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.
A short approach to chaetomellic anhydride A from2,2-dichloropalmitic acid: elucidation of the mechanism governingthe functional rearrangement of the chlorinatedpyrrolidin-2-one intermediate / Bellesia, Franco; Danieli, Chiara; L., De Buyck; R., Galeazzi; Ghelfi, Franco; Mucci, Adele; M., Orena; Pagnoni, Ugo Maria; A. F., Parsons; Roncaglia, Fabrizio. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 62:4(2006), pp. 746-757. [10.1016/j.tet.2005.09.140]
A short approach to chaetomellic anhydride A from2,2-dichloropalmitic acid: elucidation of the mechanism governingthe functional rearrangement of the chlorinatedpyrrolidin-2-one intermediate
BELLESIA, Franco;DANIELI, Chiara;GHELFI, Franco;MUCCI, Adele;PAGNONI, Ugo Maria;RONCAGLIA, Fabrizio
2006
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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