Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (+/-)-N-benzyl-coerulescine and (+/-)-horsfiline

Jennifer E. Thomson, Andrew F. Kyle, Kenneth B. Ling, Siobhan R. Smith, Alexandra M. Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (+/-)-N-benzylcoerulescine and (+/-)-horsfiline. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3801-3813
Number of pages13
JournalTetrahedron
Volume66
Issue number21
DOIs
Publication statusPublished - 22 May 2010

Keywords

  • Lewis-base catalysis
  • N-heterocyclic carbene
  • Organocatalysis
  • Carboxyl transfer
  • Spiro[pyrrolidine-3,3 '-oxindole]
  • N-HETEROCYCLIC CARBENE
  • HIGHLY ENANTIOSELECTIVE SYNTHESIS
  • MAMMALIAN-CELL CYCLE
  • OXINDOLE ALKALOIDS
  • PROCHIRAL NUCLEOPHILES
  • DISUBSTITUTED KETENES
  • ASPERGILLUS-FUMIGATUS
  • ASYMMETRIC-SYNTHESIS
  • SPIROTRYPROSTATIN-B
  • RADICAL CYCLIZATION

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