Stereocontrolled Total Synthesis of (−)-Ephedradine A (Orantine)
- 14 June 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (27), 8112-8113
- https://doi.org/10.1021/ja036011k
Abstract
The stereocontrolled total synthesis of (-)-ephedradine A has been accomplished. The synthesis features an asymmetric C-H insertion reaction, an intramolecular ester-amide exchange reaction, and a Sharpless asymmetric aminohydroxylation reaction. Construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction.Keywords
This publication has 19 references indexed in Scilit:
- Efficient macrocyclization by means of 2-nitrobenzenesulfonamide and total synthesis of lipogrammistin-ATetrahedron, 2002
- Efficient Synthesis of Medium-Sized Cyclic Amines by Means of 2-NitrobenzenesulfonamideSynlett, 2002
- Recent progress in asymmetric intermolecular CH activation by rhodium carbenoid intermediatesJournal of Organometallic Chemistry, 2001
- Highly Versatile Synthesis of Nitrogen-Containing Compounds by Means of Nitrobenzenesulfonamides.Journal of Synthetic Organic Chemistry, Japan, 2001
- Asymmetric Intermolecular Carbenoid C−H Insertions Catalyzed by Rhodium(II) (S)-N-(p-Dodecylphenyl)sulfonylprolinateJournal of the American Chemical Society, 1997
- Spermine Alkaloids from Schweinfurthia papilionaceaJournal of Natural Products, 1990
- Total synthesis of (.+-.)-O-methylorantineJournal of the American Chemical Society, 1985
- The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural ProductsSynthesis, 1981
- Beitrag zur absoluten Konfiguration der Spermin‐Alkaloide O‐Methylorantin und Aphelandrin. 175. Mitteilung über organische NaturstoffeHelvetica Chimica Acta, 1979
- Structure of ephedradine A, a hypotensive principle of Ephedra rootsTetrahedron Letters, 1979