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
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- English
- Classification
- Chemistry
- License
- License undefined
- Identifiers
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- RERO DOC 22486
- DOI 10.1039/c0ob00895h
- Persistent URL
- https://folia.unifr.ch/unifr/documents/301888
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