Total Synthesis of Dixiamycin B by Electrochemical Oxidation

Rosen, Brandon R.; Werner, Erik W.; O’Brien, Alexander G.; Baran, Phil S.

doi:10.1021/ja5013323

Cited by 320 publications

(198 citation statements)

References 44 publications

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“…Though there are no current studies indicating useful pharmacological applications of the two atropdiastereomers, the remarkable stability of their N-N axes to acid, UV irradiation and heat could be utilised in the future. 81 …”

Section: Dixiamycins: Atropisomeric N-c and N-n Coupled Dimers From Mmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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. (2015). A twist of nature-the significance of atropisomers in biological systems. Natural Product Reports: a journal of current development in bioorganic chemistry, 32 (11), 1562-1583. A twist of nature-the significance of atropisomers in biological systems AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized. AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

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Section: Dixiamycins: Atropisomeric N-c and N-n Coupled Dimers From Mmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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“…Under these conditions, an 80% yield of 1-amino indole was isolated. The reaction did not proceed without catalyst or when using highly acidic Bi(OTf) 3 or TfOH catalysts (entries [4][5][6]. Weaker Brønsted acids are superior catalysts, with TFA giving just 25% yield while acetic acid provides the product in 63% yield (entries 7, 8).…”

mentioning

confidence: 99%

Synthesis of N-aryl-1-aminoindoles via intermolecular redox amination

Ramakumar

Tunge

2014

Chem. Commun.

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A redox amination strategy was developed for the synthesis of N-aryl-1-aminoindoles by N-N bond formation. Reaction of nitrosobenzenes with readily available indolines using Brønsted acid catalysis allows N-N bond formation under mild conditions. This method exploits the inherent reducing power of indoline to synthesize biologically relevant molecular architectures via redox amination. A one-pot synthesis of 1-aminoindoles starting from simple aniline and indolines is likewise described.

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“…[146] One remarkable example is the NÀNh eteroatom coupling of carbazoles at acarbon anode,investigated by Baran and co-workers as ap ivotal step of the first total synthesis of dixiamycin B( Scheme 51). [147] Thea uthors demonstrated that this reaction can be generally applied to substituted carbazoles and b-carbolines with yields of up to 66 %. Here,the electrochemical approach was superior to classic organic oxidation reactions.I nt his protocol, the supporting electrolyte (Et 4 NBr) acted as am ediator,r esulting in am ild oxidative reaction.…”

Section: Electrochemical Dehydrodimerizationmentioning

confidence: 99%

“…NÀNdehydrodimerization reaction of xiamycinAto dixiamycin B. [147] Scheme 52. Postulated mechanism for anodic cyclizations of olefins.…”

Section: Synthesis By Electrochemically Initiated Cyclizationmentioning

confidence: 99%

Elektrifizierung der organischen Synthese

et al. 2018

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Die direkte Nutzung von Elektrizität für die organische Synthese erlebt derzeit eine Renaissance. Von den eher syntheseorientierten Laboratorien, die auf diesem Gebiet arbeiten, werden neuartige oder althergebrachte Konzepte genutzt, um den Weg von der Nischentechnologie zu breiteren Anwendungen zu ebnen. Da nur Elektronen als Reagens genutzt werden, wird die Bildung von Abfallreagentien effizient vermieden. Darüber hinaus können stöchiometrische Reagentien regeneriert werden und ermöglichen eine elektrokatalysierte Umsetzung. Die Anwendung von elektroorganischen Transformationen ist jedoch mehr als nur die Minimierung des Abfallaufkommens; sie führt vielmehr zu inhärent sicheren Prozessen, zur Abkürzung vieler Synthesestufen, zu milderen Reaktionsbedingungen, zu alternativen Zugängen zu gewünschten Struktureinheiten sowie zur Schaffung neuer Bereiche für geistiges Eigentum (Patente). Wenn die verwendete Elektrizität aus regenerativen Ressourcen stammt, kann dieser Stromüberschuss direkt als terminales Oxidations‐ oder Reduktionsmittel eingesetzt werden, was eine äußerst nachhaltige und damit hochattraktive Technologie darstellt. Dieser Aufsatz gibt einen Überblick über die jüngsten Entwicklungen auf dem Gebiet der elektrochemischen Synthese, welche die Zukunft dieses stark aufstrebenden Gebietes beeinflussen werden.

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Total Synthesis of Dixiamycin B by Electrochemical Oxidation

Cited by 320 publications

References 44 publications

A twist of nature – the significance of atropisomers in biological systems

A twist of nature – the significance of atropisomers in biological systems

Synthesis of N-aryl-1-aminoindoles via intermolecular redox amination

Elektrifizierung der organischen Synthese

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