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Synfacts 2009(10): 1108-1108  
DOI: 10.1055/s-0029-1217924
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Indium Bromide Catalyzed Aziridinyl Polyene Cyclization

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
Y.-J. Zhao, L.-J. S. Tan, B. Li, S.-M. Li, T.-P. Loh*
Nanyang Technological University, Singapore
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

Aziridine-initiated polyene cyclization similar to the process mediated by 2,3-oxidosqualene cyclase can be a useful approach ­towards a number of biologically interesting aza-terpenes. This paper shows the first example of such a transformation mediated by a catalytic amount of Lewis acid. The developed protocol provides easy access to chiral terpenoid compounds containing a 3-amino group in the A ring.