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Synfacts 2008(11): 1133-1133  
DOI: 10.1055/s-0028-1083415
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Nangustine

Contributor(s): Philip Kocienski, Indu Dager
O. J. Kokas, M. G. Banwell*, A. C. Willis
The Australian National University, Canberra, Australia
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Publication History

Publication Date:
23 October 2008 (online)

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Significance

(-)-Nangustine, a member of the montanine alkaloid family, is isolated from the bulbs of Narcissus angustifolius subsp. transcarpathicus. It shows selective activity against Trypanosoma brucei rhodesiense, Trypanosoma cruzi and Plasmodium falciparum. Other members of this family also show anxiolytic, antidepressive, anticonvulsive and hypotensive properties. A Pic­tet-Spengler reaction is used to introduce C6 and to assemble the 5,11-methanomorphanthridin-one framework in (+)-nangustine.