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Synfacts 2007(9): 0901-0901  
DOI: 10.1055/s-2007-968834
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Lepadiformine

Contributor(s): Philip Kocienski, Stewart Eccles
J. J. Caldwell, D. Craig*
Imperial College London, UK
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

Lepadiformine has modest activity towards small-cell lung carcinoma and it is also a cardiac-K+-channel blocker. The key step in this synthesis is a highly diastereoselective 5-endo-trig cyclization of the (E)-vinylsulfone intermediate E to give the pyrrolidine F as a single diastereoisomer.