Synthetic studies on amphidinolides C and F: synthesis of the C18–C29 segment of amphidinolide F

Armstrong, Alan; Pyrkotis, Constantina

doi:10.1016/j.tetlet.2009.02.093

Cited by 38 publications

(18 citation statements)

References 32 publications

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“…Glutardialdehyde has been commercially available. Malondialdehyde and succinaldehyde were given by acidic reaction of malonaldehyde bisdimethylacetal and of 2,5‐dimethoxytetrahydrofuran, respectively . Finally, adipaldehyde resulted from the reaction of cyclohexane epoxide with sodium metaperiodate in THF at room temperature .…”

Section: Resultsmentioning

confidence: 99%

“…Commercial reagents were used without further purification. Succinaldehyde was given by the treatment of 2,5‐dimethoxytetrahydrofuran with hydrochloric acid in THF after stirring under reflux for 2 h according to literature . Adipaldehyde resulted from the sodium metaperiodate oxidation of cyclohexane epoxid in THF at room temperature following literature .…”

Section: Methodsmentioning

confidence: 99%

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Novel Tetraindoles and Unexpected Cycloalkane Indoles from the Reaction of Indoles and Aliphatic Dialdehydes

Sayed

Mahmoud

Heinemann

et al. 2015

Journal of Heterocyclic Chem

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The reaction of indoles with dialdehydes was studied for the first time. Mild reaction conditions using glacial acetic acid led to two novel kinds of reaction products: one designated as alkyl chain‐connected tetraindoles and the other one as bis(indolyl)‐substituted cycloalkane indoles. The suggested reaction pathways are discussed. The indole substituents of the cycloalkane indoles were either trans or cis orientated depending from the alkyl chain length.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Novel Tetraindoles and Unexpected Cycloalkane Indoles from the Reaction of Indoles and Aliphatic Dialdehydes

Sayed

Mahmoud

Heinemann

et al. 2015

Journal of Heterocyclic Chem

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“…The bisindole tetrahydrocarbazoles were obtained by the reaction of indole 1 and succinaldehyde 2 in acetic acid under mild conditions at room temperature. The succinaldehyde was freshly prepared from 2,5-dimethoxyfurane by a hydrochloric acid treatment under heating at 60 °C [ 31 ].…”

Section: Resultsmentioning

confidence: 99%

“…As indole and a monoaldehyde are known to given bisindolyl methane derivatives [ 30 , 31 ], it is suggested that one of the aldehyde functions of the succinaldehyde first reacted with two indole compounds at the electrophilic 3-position of each indole, similar to the reaction of those bisindolyl methane compounds ( Scheme 1 ). Then, the second aldehyde function reacted with the third indole at the corresponding 3-position.…”

Section: Resultsmentioning

confidence: 99%

Novel Small-Molecule Hybrid-Antibacterial Agents against S. aureus and MRSA Strains

Gehrmann

Hertlein²,

Hopke³

et al. 2021

Molecules

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Ongoing resistance developments against antibiotics that also affect last-resort antibiotics require novel antibacterial compounds. Strategies to discover such novel structures have been dimerization or hybridization of known antibacterial agents. We found novel antibacterial agents by dimerization of indols and hybridization with carbazoles. They were obtained in a simple one-pot reaction as bisindole tetrahydrocarbazoles. Further oxidation led to bisindole carbazoles with varied substitutions of both the indole and the carbazole scaffold. Both the tetrahydrocarbazoles and the carbazoles have been evaluated in various S. aureus strains, including MRSA strains. Those 5-cyano substituted derivatives showed best activities as determined by MIC values. The tetrahydrocarbazoles partly exceed the activity of the carbazole compounds and thus the activity of the used standard antibiotics. Thus, promising lead compounds could be identified for further studies.

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“…For the preparation of the 1,5‐diene precursor 2 there is a set of straightforward published methods available (Scheme ). One could either use an olefination strategy of succinic aldehyde ( 3 ) (e.g., accessible from butane‐1,4‐diol by alcohol oxidation,,,– ozonolysis of ( Z , Z )‐cycloocta‐1,5‐diene ( 4 ), or from 2,5‐dimethoxytetrahydrofuran by acetal hydrolysis,) or conduct a cross metathesis using ( Z , Z )‐cycloocta‐1,5‐diene ( 4 ) or 1,5‐hexadiene ( 5 ) and ethyl acrylate ( 6 ) (Scheme ). For our purpose, we found the latter route to be most convenient because it delivered the desired E , E ‐isomer 2 in high yield and excellent double‐bond stereoselectivity .…”

Section: Resultsmentioning

confidence: 99%

An Aged Precatalyst Solution Leads to High Catalytic Activity: Oxidative Cyclization of 1,5‐Dienes Using ppm Amounts of Ruthenium

2016

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The ruthenium tetroxide catalyzed direct oxidative cyclization is a powerful synthetic method for the diastereoselective preparation of THF diols from simple achiral 1,5‐diene starting materials with significant relevance to target‐oriented and natural product synthesis. We here report that an aged precatalyst solution exhibits an extraordinarily high reactivity. Thus, even at 50 ppm catalyst loading, impressive results were achieved with good to high yields and excellent diastereoselectivities for the four stereogenic centers that were established in this single‐step transformation. Turnover numbers of up to 15 000 and turnover frequencies of up to 3660 h−1 were obtained. The ageing effect was analyzed spectroscopically and a preliminary hypothesis to explain the reactivity is given. Finally, the generality of this effect in oxidative cyclization chemistry was demonstrated by using a set of substrates with different substitution patterns and different geometries of the reacting double bonds.

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Synthetic studies on amphidinolides C and F: synthesis of the C18–C29 segment of amphidinolide F

Cited by 38 publications

References 32 publications

Novel Tetraindoles and Unexpected Cycloalkane Indoles from the Reaction of Indoles and Aliphatic Dialdehydes

Novel Tetraindoles and Unexpected Cycloalkane Indoles from the Reaction of Indoles and Aliphatic Dialdehydes

Novel Small-Molecule Hybrid-Antibacterial Agents against S. aureus and MRSA Strains

An Aged Precatalyst Solution Leads to High Catalytic Activity: Oxidative Cyclization of 1,5‐Dienes Using ppm Amounts of Ruthenium

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