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Total synthesis of the Amaryllidaceae alkaloid clivonine

  • Haninga, Helmut Department of Organic Chemistry, University of Geneva, Switzerland
  • Giró-Mañas, Carles Department of Chemistry, Imperial College London, South Kensington campus, London, UK
  • Paddock, Victoria L. Department of Chemistry, Imperial College London, South Kensington campus, London, UK
  • Bochet, Christian G. Department of Chemistry, University of Fribourg, Switzerland - Department of Organic Chemistry, University of Geneva, Switzerland
  • White, Andrew J. P. Department of Chemistry, Imperial College London, South Kensington campus, London, UK
  • Bernardinelli, Gerald Department of Organic Chemistry, University of Geneva, Switzerland
  • Mann, Inderjit GSK Tonbridge, Old Powder Mills, Leigh, Tonbridge, Kent, UK
  • Oppolzer, Wolfgang Department of Organic Chemistry, University of Geneva, Switzerland
  • Spivey, Alan C. Department of Chemistry, Imperial College London, South Kensington campus, London, UK - Department of Organic Chemistry, University of Geneva, Switzerland
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    02.03.2011
Published in:
  • Organic & Biomolecular Chemistry. - 2011, vol. 9, p. 2809-2820
English Two syntheses of the Amaryllidaceae alkaloid clivonine (1) are described. Both employ previously reported 7-arylhydrindane 6 as an intermediate but differ in the method employed for subsequent introduction of what becomes the ring-B lactone carbonyl carbon (C7). The synthesis featuring a Bischler–Napieralski reaction for this transformation constitutes the first asymmetric synthesis of natural (+)-clivonine. Crystal structures for compounds (±)-13, (±)-16, (−)-20 and (±)-28 are also reported.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/301888
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