Selective Reduction of 7-Demethylsinomenine

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Several borohydride reagents:sodium borohydride,sodium cyanoborohydride,soudium acetoxyborohydride and soudium triacetoxyborohydride were screened,respectively,for the reduction of 7-demethylsinomenine,which was an α,β-dicarbonyl compound derived from sinomenine.Highly regio- and stereo-selectivity was acquired when sodium cyanoborohydride or NaBH(OAc)3 was used.The product was structurally confirmed as 7R configuration by NMR,X-ray crystal diffraction analysis.Some preliminary discussion was also made on the mechanism of the selective reduction.
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