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Synlett 2009(9): 1498-1500  
DOI: 10.1055/s-0029-1217172
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Sequential Allylic Transfer Strategy for the Synthesis of (-)-Adaline and (-)-Euphococcinine

Bobin Lee, Jisook Kwon, Chan-Mo Yu*
BK-21 School of Chemical Materials Science and Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea
Fax: +82(31)2907075; e-Mail: cmyu@chem.skku.ac.kr;
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Publication History

Received 29 February 2009
Publication Date:
13 May 2009 (online)

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Abstract

Enantioselective synthesis of the piperidine alkaloids, (-)-adaline (1) and (-)-euphococcinine (2), were achieved from 7 in a six-step sequence through stepwise allylic transfer reactions. Dramatic additive effect of Bu3SnF for the conversion of 3 into 9 was observed to expedite the process to afford the cyclized products in good yields.

Key words

alkaloid - allylation - chiral - cyclization - stereoselectiv­ity

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