Xanthone Natural Products via <i>N</i>-Heterocyclic Carbene Catalysis: Total Synthesis of Atroviridin

Suzuki, Yumiko; Fukuta, Yoshihisa; Ota, Sadao; Kamiya, Masayo; Sato, Masayuki

doi:10.1021/jo200303c

Cited by 29 publications

(17 citation statements)

References 31 publications

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“…[74] In dieser Reaktion wirkt ein mithilfe eines NHC erzeugtes Acylanion als Nucleophil zur nucleophilen aromatischen Substitution. [75] Sie beschrieben 2008 die NHC-vermittelte Aroylierung funktionalisierter Fluorbenzole mit Katalysatormengen von nur 1 Mol-%. [75] Sie beschrieben 2008 die NHC-vermittelte Aroylierung funktionalisierter Fluorbenzole mit Katalysatormengen von nur 1 Mol-%.…”

Section: Nhc-katalysierte Aroylierungenunclassified

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Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

et al. 2012

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Katalytische Umwandlungen mit N‐heterocyclischen Carbenen (NHCs) haben sich als effiziente Ansätze zum Aufbau komplexer Moleküle erwiesen. Seit der Veröffentlichung von Stetter 1975 zur Totalsynthese von cis‐Jasmon und Dihydrojasmon durch Carbenkatalyse hat sich die Anwendung von NHCs in der Totalsynthese, insbesondere in den letzten zehn Jahren, schnell verbreitet. Dieser Aufschwung ist zweifellos die Folge neuerer Entwicklungen bei NHC‐katalysierten Reaktionen, einschließlich der neuen Benzoin‐, Stetter‐, Homoenolat‐ und Aroylierungsprozesse. Die Umwandlungen ermöglichen ebenso typische wie auf Umpolung beruhende Bindungsbildungen und sind bereits als Schlüsselschritte in mehreren neuen Totalsynthesen aufgetreten. Dieser Kurzaufsatz beschreibt diese neuen Arbeiten und zeigt die verstärkten Einsatzmöglichkeiten der Carbenkatalyse in der Totalsynthese auf.

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Section: Nhc-katalysierte Aroylierungenunclassified

“…In den letzten 20 Jahren haben Miyashita, Suzuki und Mitarbeiter diese Reaktion zu einer allgemeinen Methode für die Synthese von aroylierten Verbin-dungen entwickelt. [75] Sie beschrieben 2008 die NHC-vermittelte Aroylierung funktionalisierter Fluorbenzole mit Katalysatormengen von nur 1 Mol-%. [76]…”

Section: Nhc-katalysierte Aroylierungenunclassified

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

et al. 2012

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“…2 Two elegant syntheses of 2 have been reported recently by Theodorakis 3 and Suzuki. 4 Representative of more complex xanthones is the angularly-fused, heptacyclic xanthone cervinomycin A 5 ( 3 ), which exhibits potent activity against numerous bacterial strains and has been prepared twice by total synthesis. 6 …”

Section: Introductionmentioning

confidence: 99%

Concise approach to 1,4-dioxygenated xanthones via novel application of the Moore rearrangement

2012

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The rapid synthesis of 1,4-dioxygenated xanthones and related natural products employing the Moore rearrangement as a key transformation has been developed. The approach features an acetylide stitching step to unite a substituted squaric acid with a protected hydroxy benzaldehyde derivative to provide a key intermediate that undergoes facile Moore rearrangement to deliver a hydroxymethyl aryl quinone. Subsequent oxidation, hydroxy group deprotection and cyclization then affords highly functionalized xanthones. The utility of the approach was demonstrated by its application to a concise and efficient synthesis of the naturally-occurring xanthone 1. The structure of a natural product that had been named dulcisxanthone C was also corrected to that of the xanthone 1.

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“…The majority of multi‐component reactions were performed between carbonyl containing compounds and different groups of nucleophilic reagents via classical condensations in the presence of a catalytic system . One such example is the synthesis of various xanthene derivatives , as a very interesting class of oxygen‐containing heterocycles. Development of a variety of compounds based on xanthene nucleus with potential applications in pharmaceutical chemistry , material science , and also industrial technologies is an active ongoing research area.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of a new porous organic polymer equipped with N‐propyl sulfamic acid functionalities: As an efficient heterogeneous catalyst for the synthesis of 1,8‐dioxo‐octahydroxanthene derivatives

Mouradzadegun

Mostafavi

2017

Polymer Engineering & Sci

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The manuscript reports the synthesis of a polymeric calix[4]resorcinarene catalyst incorporated with N‐propyl sulfamic acid and the catalytic synthesis of 1,8‐dioxo‐octahydroxanthenes by this polymeric catalyst. Highly cross‐linked porous organic polymers as a class of amorphous and nano‐scale porous polymeric networks have been playing a key role in the development of organic synthesis and catalytic systems. The catalyst synthetic steps include (1) the synthesis of calix[4]resorcinarene, (2) polymerization with formaldehyde, (3) modification with 3‐(triethoxysilyl)propylamine (APTES), and finally (4) modification in the presence of chlorosulfonic acid to produce an efficient heterogeneous acidic catalyst for being applied in the condensation reaction of dimedone with divergent aryl aldehydes for synthesizing a series of 1,8‐dioxo‐octahydroxanthenes. This newly synthesized catalyst was characterized by some spectroscopic methods such as Fourier‐Transform Infrared spectroscopy (FT‐IR), elemental analysis (CHNS), field emission scanning electron microscopy (FE‐SEM), transmission electron microscopy (TEM), gas adsorption/desorption Brunauer‐Emmett‐Teller (BET) methodology, and thermogravimetric analysis (TGA) and its recyclability was successfully proved. Solvent‐free conditions, easy reaction handling and work up, mild acidic conditions, green and affordable methodology, gaining high yields of products in short reaction times, and also the catalyst reusability, are the most important advantages of the present method. POLYM. ENG. SCI., 58:1362–1370, 2018. © 2017 Society of Plastics Engineers

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Xanthone Natural Products via N-Heterocyclic Carbene Catalysis: Total Synthesis of Atroviridin

Cited by 29 publications

References 31 publications

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

Anwendungen der Katalyse mit N‐heterocyclischen Carbenen in Totalsynthesen

Concise approach to 1,4-dioxygenated xanthones via novel application of the Moore rearrangement

Design and synthesis of a new porous organic polymer equipped with N‐propyl sulfamic acid functionalities: As an efficient heterogeneous catalyst for the synthesis of 1,8‐dioxo‐octahydroxanthene derivatives

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