Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids Journal Article


Authors: Carra, R. J.; Epperson, M. T.; Gin, D. Y.
Article Title: Application of an intramolecular dipolar cycloaddition to an asymmetric synthesis of the fully oxygenated tricyclic core of the stemofoline alkaloids
Abstract: An intramolecular non-stabilized azomethine ylide dipolar cycloaddition was applied toward the first non-racemic synthesis of the fully oxygenated bridged pyrrolizidine core (45) of (+)-stemofoline (1) in 11 steps from a commercially available starting material. © 2008 Elsevier Ltd. All rights reserved.
Keywords: unclassified drug; drug structure; nuclear magnetic resonance spectroscopy; stereochemistry; cycloaddition; asymmetric synthesis; alkaloid derivative; pyrrolizidine alkaloid; stemofiline; hydrogenolysis
Journal Title: Tetrahedron
Volume: 64
Issue: 17
ISSN: 0040-4020
Publisher: Elsevier Inc.  
Date Published: 2008-04-21
Start Page: 3629
End Page: 3641
Language: English
DOI: 10.1016/j.tet.2008.02.008
PROVIDER: scopus
PMCID: PMC2352155
PUBMED: 18443655
DOI/URL:
Notes: --- - "Cited By (since 1996): 8" - "Export Date: 17 November 2011" - "CODEN: TETRA" - "Source: Scopus"
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  1. David Y Gin
    41 Gin
  2. Ryan J Carra
    1 Carra