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Issue 19, 1969
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Studies on the syntheses of heterocyclic compounds. Part CCCXV. Modified total synthesis of (±)-galanthamine through phenol oxidation

T. Kametani,  K. Yamaki,  H. Yagi  and  K. Fukumoto 

Abstract

Oxidation of 2-bromo-5-hydroxy-N-(4-hydroxyphenethyl)-4-methoxy-N-methylbenzamide (VIII) with ferricyanide afforded the narwedine-type enone (X) in an excellent yield (40%). Reduction of (X) with lithium aluminium hydride gave (±)-galanthamine (II) and (±)-epigalanthamine (XXI) in yields of 50 and 40% respectively. Oxidation of (II) with manganese dioxide afforded (±)-narwedine (XIX) This work also constitutes a formal synthesis of (±)-lycoramine.

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Article type: Paper
DOI: 10.1039/J39690002602
Citation: J. Chem. Soc. C, 1969,0, 2602-2605
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    Studies on the syntheses of heterocyclic compounds. Part CCCXV. Modified total synthesis of (±)-galanthamine through phenol oxidation

    T. Kametani, K. Yamaki, H. Yagi and K. Fukumoto, J. Chem. Soc. C, 1969, 0, 2602
    DOI: 10.1039/J39690002602

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