An Improvement of the Aluminium Iodide Method for Ether Cleavage: Catalysis by Quaternary Ammonium Iodides

Andersson, Sven

doi:10.1055/s-1985-31235

Cited by 25 publications

(9 citation statements)

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“…For some additional metabolites (products A through G), standards were not available. These products were characterized by GC-MS, by 1 H NMR, and (partially) by comparison with literature data (products B and G).…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

Gesell

Hammer

Specht

et al. 2001

Appl Environ Microbiol

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We examined the pathway by which the fungicide biphenyl is metabolized in the imperfect fungus Paecilomyces lilacinus. The initial oxidation yielded the three monohydroxylated biphenyls. Further hydroxylation occurred on the first and the second aromatic ring systems, resulting in the formation of five di-and trihydroxylated metabolites. The fungus could cleave the aromatic structures, resulting in the transformation of biphenyl via ortho-substituted dihydroxybiphenyl to six-ring fission products. All compounds were characterized by gas chromatography-mass spectroscopy and proton nuclear magnetic resonance spectroscopy. These compounds include 2-hydroxy-4-phenylmuconic acid and 2-hydroxy-4-(4-hydroxyphenyl)-muconic acid, which were produced from 3,4-dihydroxybiphenyl and further transformed to the corresponding lactones 4-phenyl-2-pyrone-6-carboxylic acid and 4-(4-hydroxyphenyl)-2-pyrone-6-carboxylic acid, which accumulated in large amounts. Two additional ring cleavage products were identified as (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)-acetic acid and [5-oxo-3-(4-hydroxyphenyl)-2,5-dihydrofuran-2-yl]-acetic acid. We found that P. lilacinus has a high transformation capacity for biphenyl, which could explain this organism's tolerance to this fungicide.

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Section: Resultsmentioning

confidence: 99%

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

Gesell

Hammer

Specht

et al. 2001

Appl Environ Microbiol

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“…The one methoxy group remained unaffected by BBr 3 even after 1 d at ambient temperature. Also, treatment of rac-22 with BF 3 ·Me 2 S [40] only afforded rac-24, while a significant degree of decomposition was observed with other protocols (AlI 3 / Bu 4 NI in refluxing benzene; [41] LiSEt in DMF under microwave heating [42] ). The inertness of the methoxy group at C-7' towards demethylation becomes plausible by regarding the X-ray structure of rac-22 (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of cyclo‐Mumbaistatin Analogues through Anionic Homo‐Fries Rearrangement

Neufeind

Hülsken

Neudörfl

et al. 2011

Chemistry A European J

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The structurally unique polyketide mumbaistatin is the strongest naturally occurring inhibitor of glucose-6-phosphate translocase-1 (G6P-T1), which is a promising target for drugs against type-2 diabetes mellitus and angiogenic processes associated with brain tumor development. Despite its high relevance, mumbaistatin has so far withstood all attempts towards its total synthesis. In the present study an efficient total synthesis of a deoxy-mumbaistatin analogue containing the complete carbon skeleton and a spirolactone motif closely resembling the natural product in its cyclized form was elaborated. Key steps of the synthesis are a Diels-Alder cycloaddition for the construction of the fully functionalized anthraquinone moiety and an anionic homo-Fries rearrangement to build up the tetra-ortho-substituted benzophenone core motif, from which a spiroketal lactone forms in a spontaneous process. The elaborated strategy opens an entry to a variety of new analogs of mumbaistatin and cyclo-mumbaistatin and may be exploited for the total synthesis of the natural product itself in the future.

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“…The demethylation conversions were complete after stirring for 3 hours in benzene or cyclohexane and afforded phenols in moderate to high yields. 69,70 Extension of the substrate to 3,4,5-trimethoxybenzaldehyde and isovanillin were less satisfactory for either low isolated yields or partial deprotection. Diphenyl ether remained intact under the condition.…”

Section: Application Of Ali 3 -Tbai In Exhaustive Demethylationmentioning

confidence: 99%

Application of aluminum triiodide in organic synthesis

Tian¹,

Sang²

2015

Arkivoc

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The multifaceted reactivity of aluminum triiodide (AlI 3 ) is reviewed. The oxophilic character of the Lewis acid enables the formation of coordination complexes with esters, ethers, oxiranes, diols, Noxides, and sulfoxides that decompose spontaneously to afford acids, alcohols and olefins via ester and ether cleavage, deoxygenation of oxiranes, and deoxydehydration of diols, respectively. As an iodide ion source and hydrogen iodide precursor, the reagent allows iodination and reduction of Noxides, sulfoxides and azides as well as hydroiodination of alkenes and alkynes. Aluminum enolates, generated by treatment of -haloketones with AlI 3 , provide accesses to -hydroxy ketones, 1,5-diones, and β-iodo Morita-Baylis-Hillman esters.

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An Improvement of the Aluminium Iodide Method for Ether Cleavage: Catalysis by Quaternary Ammonium Iodides

Cited by 25 publications

References 0 publications

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products

Total Synthesis of cyclo‐Mumbaistatin Analogues through Anionic Homo‐Fries Rearrangement

Application of aluminum triiodide in organic synthesis

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