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Regioselective complexation of the dimethoxy arene ring of canadine to the Cr(CO)2 moiety gives two diastereoisomers which are separated by flash chromatography. Deprotonatlon of either diastereoisomer with n-butyllithium followed by addition of methyl iodide or trimethylsilyl chloride gives C11-methyl- or -trimethylsilylcanadine after decomplexatlon. Each diastereoisomer of the C11-trimethylsilylcanadine complex may be treated with base and methyl iodide to give, after desilylation and decomplexatlon, the enantiomerically pure (-)-(8R) and (-)-(8S) methyl canadines; racemic samples of C8-methylcanadines are prepared via an independent route. © 1988.

Original publication

DOI

10.1016/S0040-4020(01)85104-8

Type

Journal article

Journal

Tetrahedron

Publication Date

01/01/1988

Volume

44

Pages

171 - 186