LXXXIII.—Synthesis and resolution of gnoscopine (dl-narcotine)

DARK Classics in Chemical Neuroscience: Opium, a Historical Perspective

“…Beckett at the start of his long series of experiments on noscapine and its degradation products in 1875 found that it was possible to reduce noscapine into hydrocotamine ( 29 ) and 28 (Figure ). Freund was able to determine the positions of the methylenedioxy and methoxy in 26 and by comparison also 29 . , Perkin took all of the available data and pieces and decided to couple 28 and 29 to give a racemic mixture of noscapine, and upon chiral resolution, gave a small amount of pure noscapine, confirming the structure via synthesis …”

“…106,107 Perkin took all of the available data and pieces and decided to couple 28 and 29 to give a racemic mixture of noscapine, and upon chiral resolution, gave a small amount of pure noscapine, confirming the structure via synthesis. 108 Narceine. Isolation.…”

Converting a Birch Reduction Product into a Polyketide: Application to the Synthesis of a C1–C11 Building Block of Rimocidin

“…Hydroxyindane 21 was methylated with Me 2 SO 4 in the presence of aqueous KOH. The resulting methoxyindane (i.e., 22 ; 91 % yield) reacted with iodine monochloride in AcOH30 to give an 83:17 mixture of monoiodo derivatives in favor of the ortho ‐substitution product 23 . This ratio was improved to 95:5 by recrystallization.…”

Über die Begleitalkaloide des Morphins. VII

“…Ausgehend von Cotarnin 1 und Mekonin 2 isolierten PERKIN und ROBINSON [3] in geringer Ausbeute a-Gnoscopin 3, das auch in die optischen Antipoden aufgespalten werden konnte.…”