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
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, F., DE BUYCK, L., Danieli, C., Galeazzi, R., Ghelfi, F., Mucci, A., Orena, M., Pagnoni, U.M., Parsons, A.F., Roncaglia, F.. - In: TETRAHEDRON. - ISSN 0040-4020. - 62:(2006), pp. 746-757. [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
GALEAZZI, ROBERTA;ORENA, MARIO;
2006-01-01
Abstract
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; RearrangementI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
