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From the same journal

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

Research output: Contribution to journalArticle

Published copy (DOI)

Author(s)

  • F Bellesia
  • C Danieli
  • L De Buyck
  • R Galeazzi
  • F Ghelfi
  • A Mucci
  • M Orena
  • U M Pagnoni
  • A F Parsons
  • F Roncaglia

Department/unit(s)

Publication details

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

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. (c) 2005 Elsevier Ltd. All rights reserved.

    Research areas

  • halocompound, pyrrolidinone, radical reaction, rearrangement, FARNESYL-PROTEIN TRANSFERASE, TRANSFER RADICAL CYCLIZATION, STEREOSELECTIVE-SYNTHESIS, DIMETHYLMALEIC ANHYDRIDE, MOLECULAR MECHANICS, EFFICIENT SYNTHESIS, FACILE SYNTHESIS, GAMMA-LACTAMS, CUCL-TMEDA, ANALOGS

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