The Synthesis of Ventiloquinone F and Isoventiloquinone F as Racemates

Giles, Robin G. F.; Green, Ivan R.; Eeden, Nestor van

doi:10.1002/ejoc.200400489

Cited by 16 publications

(7 citation statements)

References 24 publications

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“…In particular, the use of a facile naphthalene synthesis was a focus. The synthesis of naphthols from aryl aldehydes via a Stobbe condensation/cyclization sequence is such a process and, to our delight, had previously been elucidated by Green and co-workers . A modification of their protocol readily gave us 17 (Scheme ) in two steps and up to 81% yield from commercially available 2,4,5-trimethoxybenzaldehyde ( 15 ).…”

Section: Resultsmentioning

confidence: 99%

A Concise Synthesis of the Naphthalene Portion of Purpuromycin

2008

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A concise synthesis of naphthalene compounds for incorporation into a synthetic sequence for the rubromycin family of natural products is presented. These highly substituted naphthalenes are generated in seven and nine steps, respectively, from 2,4,5-trimethoxybenzaldehyde. Three ring-forming methods were explored and the controlled oxygenation of different positions was investigated to yield differentially substituted/protected systems. Key steps to the final products include a Stobbe condensation to form the ring system and a novel series of regioselective oxidations to introduce the required oxygen functionality. These naphthalene products incorporate orthogonal protecting groups and are suitable for combination with a variety of coupling partners.

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Section: Resultsmentioning

confidence: 99%

A Concise Synthesis of the Naphthalene Portion of Purpuromycin

2008

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“…One particularly difficult transformation in organic synthesis is the decarboxylation of aromatic systems. Often, the chemistry to form aromatic systems takes advantage of the reactivity of carboxylates, which frequently results in their incorporation as carboxylate substituents in the products. − In contrast to aliphatic systems, the lack of stabilization in the intermediates formed during aromatic decarboxylation renders the process unfavorable.…”

Section: Introductionmentioning

confidence: 99%

Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps

et al. 2013

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Mechanism studies of a mild palladium catalyzed decarboxylation of aromatic carboxylic acids are described. In particular, reaction orders and activation parameters for the two stages of the transformation were determined. These studies guided development of a catalytic system capable of turnover. Further evidence reinforces that the second stage, protonation of the aryl palladium intermediate, is the rate-determining step of the reaction. The first step, decarboxylative palladation is proposed to occur through an intramolecular electrophilic palladation pathway, which is supported by computational and mechansim studies. In contrast to the reverse reaction (C-H insertion), the data support an electrophilic aromatic substitution mechanism involving a stepwise intramolecular protonation sequence for the protodepalladation portion of the reaction.

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“…Other patents relate PTK787 to a specific method of treatment. Novartis, Dana Farber, and Academisch Zeikenhuis Groningen maintain patents that propose the use of PTK787 in the treatment of myeloma, ocular neovascular disease [109], angiogenic myeloid metaplasia [110], and mesothelioma [111].…”

Section: Ptk787 (1-[4-chloroanilino]-4-[pyridylmethyl]mentioning

confidence: 99%

Ribonucleotide Reductase: A Critical Enzyme for Cancer Chemotherapy and Antiviral Agents

Cerqueira¹,

Ramos²

2007

PRA

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Ribonucleotide Reductase (RNR) plays a critical role in DNA synthesis, and is a well-recognized target for cancer chemotherapeutic and antiviral agents. RNR inhibition precludes DNA transcription and repair, from which results cell apoptosis. Many regulation checkpoints concerning RNR activity have been unravelled through the last two decades, with potential use to inhibit enzyme activity. This was accomplished by researchers from different but complementary areas, and from which several and different inhibitors have resulted. The volume of these studies has generated over 4000 articles since the discovery of RNR in 1960. This review summarises patents and papers during the period 1958 - 2005 dealing with the present understanding of ribonucleotide reductase biochemistry, mechanism of action and the most relevant data concerning RNR inhibition. Special attention is given to the inhibitors that have been patented and are currently in clinical use.

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The Synthesis of Ventiloquinone F and Isoventiloquinone F as Racemates

Cited by 16 publications

References 24 publications

A Concise Synthesis of the Naphthalene Portion of Purpuromycin

A Concise Synthesis of the Naphthalene Portion of Purpuromycin

Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps

Ribonucleotide Reductase: A Critical Enzyme for Cancer Chemotherapy and Antiviral Agents

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