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Synfacts 2009(11): 1192-1192  
DOI: 10.1055/s-0029-1218023
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Adaline

Contributor(s): Philip Kocienski, Indu Dager
B. Lee, J. Kwon, C.-M. Yu*
Sungkyunkwan University, Suwon, Korea
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

The alkaloids (-)-adaline and (-)-euphococcinine are insect repellants found in the defense secretions of the ladybug. Key steps in the synthesis depicted are (1) an intermolecular asymmetric allylation reaction (B → D) mediated by a chiral Lewis acid and (2) an intramolecular ­allylation reaction (F → H) used to construct the bicyclic ring system.