Studies on the Alkaloids of Menispermaceous Plants. CI. : Alkaloids of Cocculus laurifolius DC. (Suppl. III)

Tomita, Masaru; Kusuda, Fuyuki

doi:10.1248/cpb1953.1.1

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1963

1989

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Cited by 19 publications

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“…The free base corresponding to this alkaloid salt has not yet been found in nature. X" XIII Laurifoline, the first quaternary aporphine to be isolated from nature, was obtained by Tomita and Kusuda together with coclaurine, trilobine, and coclanoline from Cocculus laurifolius (141). The chloride is readily soluble in water and hot alcohol, but is insoluble in less polar organic solvents.…”

Section: Quaternarymentioning

confidence: 99%

The Aporphine Alkaloids

Shamma¹,

Slusarchyk²

1964

Chem. Rev.

117

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Section: Quaternarymentioning

confidence: 99%

The Aporphine Alkaloids

Shamma¹,

Slusarchyk²

1964

Chem. Rev.

117

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Oxydative Kondensationen quartärer phenolischer Basen

Franck¹,

Blaschke²,

Schlingloff³

1963

Angewandte Chemie

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Einfache phenolische Basen können in Anlehnung an die Biosynthese mit guter Ausbeute oxydativ zu Alkaloiden der Isochinolin‐Gruppe kondensiert werden, wenn deren Stickstoff quartär ist. Auf diese Weise wurden mehr als 60 Alkaloide verschiedener Strukturtypen besser zugänglich. Von den zahlreichen möglichen Kondensationen der zwischendurch gebildeten mesomeren Radikale erfolgten dabei nur diejenigen, die zu natürlichen Alkaloiden führen. Die Befunde lassen vermuten, daß die oxydative Kondensation quartärer Basen auch bei der Alkaloid‐Biosynthese in der Pflanzenzelle eine Rolle spielt.

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Oxidative Condensation of Quaternary Phenolic Bases

Franck¹,

Blaschke²,

Schlingloff³

1964

Angew. Chem. Int. Ed. Engl.

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Provided they contain quaternary nitrogen, simple phenolic bases can undergo oxidative condensation under conditions similar to those of biogenesis to form alkaloids of the isoquinoline series with good yields. By means of such oxidative condensations, more than sixty alkaloids of various structural types have become more easily obtainable. Of the numerous possible condensations of the intermediate mesomeric radicals only those which Iead to naturally occurring alkaloids give good yields and few by-products. The resuits suggest that oxidative condensations of quaternary bases are also involved in the biosynthesis of alkaloids in the plant cell.

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Studies on the Alkaloids of Menispermaceous Plants. CI. : Alkaloids of Cocculus laurifolius DC. (Suppl. III)

Cited by 19 publications

References 0 publications

The Aporphine Alkaloids

The Aporphine Alkaloids

Oxydative Kondensationen quartärer phenolischer Basen

Oxidative Condensation of Quaternary Phenolic Bases

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