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Synfacts 2006(8): 0751-0751  
DOI: 10.1055/s-2006-941929
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Lepadiformine

Contributor(s): Philip Kocienski, Thomas Snaddon
M. Lee, T. Lee, E.-Y. Kim, H. Ko, D. Kim, S. Kim*
Seoul National University, Korea
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

Isolated from Clavelina lepidaforma, the perhydropyrrolo[2,1-j]quinolone alkaloid (-)-lepadiformine displays cytotoxic activity and cardiovascular effects. Noteworthy in this synthesis is the use of a substrate-controlled Ireland-Claisen rearrangement to create two new con­tiguous stereocenters.