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, Roberta; Ghelfi, F.; Mucci, A.; Orena, Mario; 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; Rearrangement
2006
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11566/53195
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