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Synfacts 2010(11): 1216-1216  
DOI: 10.1055/s-0030-1258713
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Hexahydroapoerysopine

Contributor(s): Steven V. Ley, Catherine F. Carter
Y.-M. Zhao, P. Gu, Y.-Q. Tu*, H.-J. Zhang, Q.-W. Zhang, C.-A. Fan
Lanzhou University, P. R. of China
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Publication History

Publication Date:
21 October 2010 (online)

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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.