Transition metal complexes in organic synthesis. Part 65: Iron-mediated synthesis of carazostatin, a free radical scavenger from Streptomyces chromofuscus, and O-methylcarazostatin

Knölker, Hans‐Joachim; Hopfmann, Thomas

doi:10.1016/s0040-4020(02)01180-8

Cited by 39 publications

(9 citation statements)

References 35 publications

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“…Free radical scavenger, carbazostatin (76) isolated from Streptomyces chromofuscus, 50 has been synthesised from cyclohexa-1,3-diene (77) and 2-heptyl-4-methoxy-3-methylaniline (78), which was prepared in seven steps from 1-nonyne (79) (Scheme 14). 51 The key step of the synthesis is iron-mediated oxidative cyclisation of 80 to afford 76. Carbazostatin shows a strong inhibition of the lipid peroxidation induced by free radicals.…”

Section: Carbazolesmentioning

confidence: 99%

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

2004

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Section: Carbazolesmentioning

confidence: 99%

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

2004

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“…The reaction proceeded well with heptaldehyde 16e , providing the desired product 3r in 75% yield (Table ). Inspired by the result, we carried out the acylation of carbazole 15 with heptaldehyde 16e to synthesize the acyl precursor 18 of carbazole alkaloid carazostatin . The acylation provided exclusively the regioisomeric acyl derivative 17e in 70% yield (Table ).…”

Section: Resultsmentioning

confidence: 99%

Site-Selective Aerobic C–H Monoacylation of Carbazoles Using Palladium Catalysis

2020

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This manuscript describes the development of a remarkably general palladium-catalyzed monoacylation of carbazoles using toluene derivatives playing the dual role of acyl source and organic solvent. The method uses NHPI as the cocatalyst and oxygen as the sole oxidant. Interestingly, the acylation of monosubstituted N-pyridylcarbazoles takes place regioselectively at the C-8 position. The scope of the method is explored using aldehyde as the acyl source. This highly site-selective acylation proceeds through a radical process.

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“…albofungin antibiotic [281] chloroalbofungin antibiotic [281] chrestoxanthones A-C antifungal [281] Streptomyces chromofuscus carazostatin carbazole alkaloids [282] Streptomyces chromofuscus herboxidiene bioactive compound [283] Streptomyces cinnamonensis 2-demethylmonensihs A, B minor congeners of monensins [284] arcyriaflavin E indolocarbazole alkaloid [285] endophenazine A antimicrobial compound [286,287] …”

Section: Streptomyces Chrestomyceticusmentioning

confidence: 99%

Section: Streptomyces Chrestomyceticusmentioning

confidence: 99%

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

Benito

Ibáñez

Moncho

et al. 2017

EFSA Supporting Publications

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The present work constitutes the external scientific report of the EFSA open call OC/EFSA/FEED/2015/01. The aim of the call was to provide EFSA with a database from a review on the taxonomical description and potential toxigenic capacities of microorganisms used for the industrial production of feed additives and food enzymes. The review includes microorganisms used as source of feed additives and food enzymes for which EFSA has received or can potentially receive applications for safety assessment, and which have not been recommended for Qualified Presumption of Safety status. The database also comprises the molecular taxonomical identifiers and biosynthetic pathways involved in the production of toxic compounds and the responsible genes. The main result of the project is shown as a database developed according to the EFSA data structure. The methodological aspects and the queries used in the systematic search, as well as the procedure applied for the screening of scientific documents retrieved are described in this report. Details are available in supplementary appendices.In total, 22970 scientific documents were screened in the literature search, from which 411 were initially selected for providing pertinent data for the scope of the project. From the review of the selected articles, 474 bioactive secondary metabolites were recorded and 59 compounds were further studied in order to obtain data on their toxicology and the conditions in which they are produced by the microorganisms used in industrial fermentations. The database generated in this project comprises details that characterise, when available, the production conditions, genes involved and toxicity of these 59 compounds. This provides information that can be used to establish safety measures when using potentially toxigenic microorganisms in industrial fermentations Disclaimer: The present document has been produced and adopted by the bodies identified above as author(s). This task has been carried out exclusively by the author(s) in the context of a contract between the European Food Safety Authority and the author(s), awarded following a tender procedure. The present document is published complying with the transparency principle to which the Authority is subject. It may not be considered as an output adopted by the Authority. The European Food Safety Authority reserves its rights, view and position as regards the issues addressed and the conclusions reached in the present document, without prejudice to the rights of the authors. Acknowledgements:We thank the following EFSA satff: Jaime Aguilera, Margarita Aguilera-Gómez, Jane Richardson, Mario Monguidi and Davide Gibin for their valuable help and collaboration throughout the project. We also would like to thank the members of AINIA: Sonia Porta, Lidia Tomás, Joaquin Espí and Juan Antonio Nieto for providing expertise in biotechnology and molecular biology and contributing with their efforts to achieve the goals of this project, and Violeta Gómez from the University of Navarra for her colla...

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Transition metal complexes in organic synthesis. Part 65: Iron-mediated synthesis of carazostatin, a free radical scavenger from Streptomyces chromofuscus, and O-methylcarazostatin

Cited by 39 publications

References 35 publications

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Site-Selective Aerobic C–H Monoacylation of Carbazoles Using Palladium Catalysis

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

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