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Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination.

Abstract
The enantioselective synthesis of (S)-(+)-tylophorine, a potent cancer cell growth inhibitor, has been accomplished in eight steps from commercially available 3,4-dimethoxybenzyl alcohol. A copper (II)-catalyzed enantioselective intramolecular alkene carboamination was employed as the key step to construct the chiral indolizidine ring.
AuthorsWei Zeng, Sherry R Chemler
JournalThe Journal of organic chemistry (J Org Chem) Vol. 73 Issue 15 Pg. 6045-7 (Aug 1 2008) ISSN: 1520-6904 [Electronic] United States
PMID18588345 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)
Chemical References
  • Alkaloids
  • Alkenes
  • Biological Products
  • Indolizines
  • Phenanthrenes
  • tylophorine
Topics
  • Alkaloids (chemical synthesis, chemistry)
  • Alkenes (chemistry)
  • Amination
  • Biological Products (chemistry)
  • Indolizines (chemical synthesis, chemistry)
  • Molecular Structure
  • Phenanthrenes (chemical synthesis, chemistry)
  • Stereoisomerism

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