The stereospecific synthesis of (-)-(8r) and (-)-(8s)-methylcanadine

Add time:08/29/2019    Source:sciencedirect.com

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.

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