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 D. Buyck, Roberta Galeazzi, Franco Ghelfi, Adele Mucci, Mario Orena, Ugo M. Pagnoni, Andrew F. Parsons, Fabrizio Roncaglia

Research output: Contribution to journalArticle

39 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)746-757
Number of pages12
JournalTetrahedron
Volume62
Issue number4
DOIs
Publication statusPublished - Jan 23 2006

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Anhydrides
Cyclization
Acids
Atoms
Stereoisomerism
Hydrolysis
maleimide

Keywords

  • Halocompound
  • Pyrrolidinone
  • Radical reaction
  • Rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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 D.; Galeazzi, Roberta; Ghelfi, Franco; Mucci, Adele; Orena, Mario; Pagnoni, Ugo M.; Parsons, Andrew F.; Roncaglia, Fabrizio.

In: Tetrahedron, Vol. 62, No. 4, 23.01.2006, p. 746-757.

Research output: Contribution to journalArticle

Bellesia, Franco ; Danieli, Chiara ; Buyck, Laurent D. ; Galeazzi, Roberta ; Ghelfi, Franco ; Mucci, Adele ; Orena, Mario ; Pagnoni, Ugo M. ; Parsons, Andrew F. ; Roncaglia, Fabrizio. / 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. In: Tetrahedron. 2006 ; Vol. 62, No. 4. pp. 746-757.
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T2 - Elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate

AU - Bellesia, Franco

AU - Danieli, Chiara

AU - Buyck, Laurent D.

AU - Galeazzi, Roberta

AU - Ghelfi, Franco

AU - Mucci, Adele

AU - Orena, Mario

AU - Pagnoni, Ugo M.

AU - Parsons, Andrew F.

AU - Roncaglia, Fabrizio

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AB - 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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KW - Radical reaction

KW - Rearrangement

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