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Synfacts 2010(11): 1216-1216
DOI: 10.1055/s-0030-1258713
DOI: 10.1055/s-0030-1258713
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Hexahydroapoerysopine
Contributor(s):Steven V. Ley, Catherine F. CarterY.-M. Zhao, P. Gu, Y.-Q. Tu*, H.-J. Zhang, Q.-W. Zhang, C.-A. Fan
Lanzhou University, P. R. of China
One-Pot Synthesis of Aminoenone via Direct Reaction of the Chloroalkyl Enone with NaN3: Rapid Access to Polycyclic Alkaloids
J. Org. Chem. 2010, 75: 5289-5295
Lanzhou University, P. R. of China
One-Pot Synthesis of Aminoenone via Direct Reaction of the Chloroalkyl Enone with NaN3: Rapid Access to Polycyclic Alkaloids
J. Org. Chem. 2010, 75: 5289-5295
Further Information
Publication History
Publication Date:
21 October 2010 (online)
Key words
hexahydroapoerysopine - [3+2] cycloaddition -
Significance
Hexahydroapoerysopine is a polycyclic alkaloid whose tetracyclic scaffold was constructed using methodology for the synthesis of aminoenones via chloroalkyl enones and sodium azide. The key step of this short synthesis is the regioselective [3+2] cycloaddition and rearrangement to give I.
Comment
The authors’ proposed mechanism is shown (F → I); however, the reaction could also proceed via a radical cleavage and recombination process as reported (K. S. Feldman, M. R. Iyer, D. K. Hester II Org. Lett. 2006, 8, 3113).