SYNTHESIS OF PYRROLIDINONES VIA FREE-RADICAL CYCLIZATIONS - POTENTIAL APPLICATION TO THE KAINOIDS

Research output: Contribution to journalArticlepeer-review

Abstract

The tin hydride-mediated cyclisation of a range of DL-serine-derived alpha-chloro amides 1 to form pyrrolidinones has been examined. The yield and stereoselectivity of the cyclisation process was found to be markedly affected by the nature of the substituent at the site of radical generation. Thus, radicals substituted at the alpha-position by methyl, phenyl, dichloro and sulfanylphenyl substituents underwent smooth cyclisation to give excellent yields (58-95%) of a mixture of diastereoisomeric pyrrolidinones while the hydrogen-substituted congener cyclised in only 31-38% yield. This procedure has potential application to pyrrolidinone/pyrrolidine natural product synthesis and, in particular, to the kainoid amino acids.

Original languageEnglish
Pages (from-to)1945-1951
Number of pages7
JournalJournal of the Chemical Society-Perkin Transactions 1
Issue number14
Publication statusPublished - 21 Jul 1994

Keywords

  • COBALT-MEDIATED CYCLIZATION
  • ENANTIOSELECTIVE SYNTHESIS
  • CLITOCYBE-ACROMELALGA
  • (-)-ALPHA-KAINIC ACID
  • 5-MEMBERED LACTAMS
  • FORMAL SYNTHESIS
  • DERIVATIVES
  • TEMPERATURE
  • AMIDES
  • ROUTE

Cite this