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Collect. Czech. Chem. Commun. 1999, 64, 203-216
https://doi.org/10.1135/cccc19990203

Intramolecular N-Acyliminium Ion-Olefin Cyclization in the Synthesis of Optically Pure Isoquinoline Derivatives: Control of Stereochemistry and Application to Synthesis of Morphine Alkaloids

Patricia Bottari, Mary Ann A. Endoma, Tomáš Hudlický*, Ion Ghiviriga and Khalil A. Abboud

Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.

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  • Endoma‐Arias Mary Ann A., Makarova Mariia, Dela Paz Helen E., Hudlicky Tomas: An Improved First‐Generation Synthesis of ent‐Oxycodone. ChemistrySelect 2020, 5, 8241. <https://doi.org/10.1002/slct.202001320>
  • Reed Josephine W., Hudlicky Tomas: The Quest for a Practical Synthesis of Morphine Alkaloids and Their Derivatives by Chemoenzymatic Methods. Acc. Chem. Res. 2015, 48, 674. <https://doi.org/10.1021/ar500427k>
  • Saikia Anil K., Indukuri Kiran, Das Jagadish: Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D. Org. Biomol. Chem. 2014, 12, 7026. <https://doi.org/10.1039/C4OB01130A>
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  • Ghiviriga Ion, Bottari Patricia Q., Hudlicky Tomas: Elucidation of the stereochemistry of octahydroisoquinoline derivatives by NMR spectroscopy. Magn Reson Chem 1999, 37, 653. <https://doi.org/10.1002/(SICI)1097-458X(199909)37:9<653::AID-MRC511>3.0.CO;2-W>
  • Ghiviriga Ion, Bottari Patricia Q., Hudlicky Tomas: Elucidation of the stereochemistry of octahydroisoquinoline derivatives by NMR spectroscopy. Magn. Reson. Chem. 1999, 37, 653. <https://doi.org/10.1002/(SICI)1097-458X(199909)37:9<653::AID-MRC511>3.0.CO;2-W>
  • Bottari Patricia, Endoma Mary Ann A., Hudlicky Tomas, Ghiviriga Ion, Abboud Khalil A.: ChemInform Abstract: Intramolecular N‐Acyliminium Ion—Olefin Cyclization in the Synthesis of Optically Pure Isoquinoline Derivatives: Control of Stereochemistry and Application to Synthesis of Morphine Alkaloids. ChemInform 1999, 30. <https://doi.org/10.1002/chin.199931254>
  • Frey Dean A., Duan Caiming, Hudlicky Tomas: Model Study for a General Approach to Morphine and Noroxymorphone via a Rare Heck Cyclization. Org. Lett. 1999, 1, 2085. <https://doi.org/10.1021/ol991135g>