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The Polonovski–Potier reaction of trans and cis berbine (cas 131-10-2)s N-oxides was studied. The 8-cyano derivative obtained from transN-oxides were used to synthesize 8-hydroxymethyl and 8-methyl berbines. This procedure was applied to the stereocontroled synthesis of (8R, 14S)-(−)-8-methylcanadine from (14S)-(−)-canadine.
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