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Synfacts 2008(10): 1023-1023  
DOI: 10.1055/s-2008-1078189
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of ()-Stemonamine

Contributor(s): Philip Kocienski, Stewart Eccles
Y.-M. Zhao, P. Gu, Y.-Q. Tu*, C.-A. Fan, Q. Zhang
Lanzhou University, P. R. of China
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Publikationsdatum:
22. September 2008 (online)

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Significance

Stemonamine was used as a Chinese and Japanese folk medicine for the treatment of respiratory diseases and as an insecticide. It was isolated along with other members of the Stemona family from the roots of Stemona japonica. The key step in this synthesis is the use of a tandem semipinacol rearrangement-Schmidt reaction (A → D) to create the 5,7-fused bicyclic core.