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

Bobin Lee; Jisook Kwon; Chan-Mo Yu

doi:10.1055/s-0029-1217172

LETTER

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;

Abstract

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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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Referenzen

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