Sinomenine and Disinomenine. Part Ix. On Acutumine and Sinactine

Goto, Kakuji; Sudzuki, Hideo

doi:10.1246/bcsj.4.220

Cited by 53 publications

(18 citation statements)

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“…(À)-Acutumine (1) is a tetracyclic alkaloid that was first obtained from the roots of Sinomenium acutum by Goto and Sudzuki in 1929 (Scheme 1 a). [1] The related metabolite (À)-dechloroacutumine (2) was isolated from a chlorinedeficient culture of Menispermum dauricum in 1998.…”

mentioning

confidence: 99%

Total Syntheses of (−)‐Acutumine and (−)‐Dechloroacutumine

2013

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One route fits all: Syntheses of the title complex tetracyclic alkaloids are described. The routes feature the strategic application of 5‐trimethylsilylcyclopentadiene, a selective hydrostannylation of a complex enyne, a Hosomi–Sakurai cyclization to form the skeleton of the targets, an allylic formate rearrangement to construct the spirocyclopentenone rings, and a selective hydrogenation to establish the alkyl chloride functional group of (−)‐acutumine.

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mentioning

confidence: 99%

Total Syntheses of (−)‐Acutumine and (−)‐Dechloroacutumine

2013

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“…A chlorine-containing alkaloid belonging to the hasubanan family named acutumine, was isolated in 1929 by Goto and Sudzuki, [36] as a minor component of the medicinal herb Sinomenium acutum . Its structure, determined nearly fifty years later by Tomita and co-workers [37] using X-ray crystallography, revealed a highly oxygenated tetracyclic skeleton containing four contiguous stereogenic carbon atoms of which two are quaternary.…”

Section: Acutuminementioning

confidence: 99%

“…Acutumine, a chlorine‐containing alkaloid belonging to the hasubanan family was isolated in 1929 by Goto and Sudzuki as a minor component of the medicinal herb Sinomenium acutum . Its structure, determined nearly 50 years later by Tomita et al .…”

Section: Acutuminementioning

confidence: 99%

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

et al. 2016

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Strategies for the total synthesis of complex natural products that contain two or more contiguous stereogenic quarternary carbon atoms in their intricate structures are reviewed with twelve representative examples. Emphasis has been put on the methods to create quarternary carbon stereocenters, including syntheses of the same natural product from different groups, thereby showcasing diversity of thought and individual creativity. A compendium of selected natural products containing two or more contiguous stereogenic quarternary carbon atoms and key reactions in their total or partial syntheses is provided in the Supporting Information section.

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“…Acutumin, ein Chlor‐haltiges Alkaloid aus der Familie der Hasubanane, wurde 1929 durch Goto und Sudzuki als Nebenbestandteil aus der pharmazeutischen Nutzpflanze Sinomenium acutum isoliert. Seine Struktur, die beinahe fünfzig Jahre später von Tomita und Mitarbeitern röntgenographisch ermittelt wurde, enthält ein stark Sauerstoff‐haltiges, tetracyclisches Gerüst mit vier benachbarten stereogenen Kohlenstoffatomen, von denen zwei quartär sind.…”

Section: Acutuminunclassified

Strategien für die Synthese von Naturstoffen mit benachbarten stereogenen quartären Kohlenstoffatomen

et al. 2016

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Anhand zwölf repräsentativer Beispiele stellen wir in diesem Aufsatz Strategien für die Totalsynthese komplexer Naturstoffe vor, die zwei oder mehr benachbarte stereogene quartäre Kohlenstoffatomen in ihren komplexen Molekülstrukturen enthalten. Das Hauptaugenmerk liegt dabei auf den Methoden zur Konstruktion quartärer stereogener Kohlenstoffzentren, einschließlich der Synthese desselben Naturstoffs auf verschiedenen Wegen durch unterschiedliche Forschergruppen; dies soll die Vielfalt der Gedankengänge sowie die Individualität kreativer Leistungen verdeutlichen. Ein Kompendium von ausgewählten Naturstoffen mit zwei oder mehr benachbarten stereogenen quartären Kohlenstoffatomen sowie von Schlüsselreaktionen ihrer jeweiligen Total‐ oder Partialsynthesen findet sich in den Hintergrundinformationen.

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Sinomenine and Disinomenine. Part Ix. On Acutumine and Sinactine

Cited by 53 publications

References 0 publications

Total Syntheses of (−)‐Acutumine and (−)‐Dechloroacutumine

Total Syntheses of (−)‐Acutumine and (−)‐Dechloroacutumine

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

Strategien für die Synthese von Naturstoffen mit benachbarten stereogenen quartären Kohlenstoffatomen

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