Tetramethylnorbornadiene, a Versatile Alkene for Cyclopentenone Synthesis through Intermolecular Pauson–Khand Reactions

Revés, Marc; Lledó, Agustí; Ji, Yining; Blasi, Emma; Riéra, Antoni

doi:10.1021/ol301545e

Cited by 25 publications

(16 citation statements)

References 31 publications

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“…The latter is set up for cleavage by a retro-Diels-Alder cycloaddition [57] to give 2 and aromatic compound 7. Similar cleavages have been reported, [58] but this one proceeds under milder conditions.…”

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confidence: 86%

Regioselective Multicomponent Synthesis of 2,4,6‐Trisubstituted Phenols from Fischer Alkynyl Carbene Complexes

et al. 2016

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A series of 2,4,6-trisubstituted phenols 7a-7p has been prepared in moderate to good yields (23-77 %) by a retroDiels-Alder reaction from hindered tricyclic alcohols 6a-6q, using mild acidic conditions. The tricyclic alcohols were obtained by reduction of highly functionalized cyclohexadienones 5a-5q, which in turn were regioselectively prepared under mild conditions in high yields by treatment of a series of stable chromium(0) and tungsten(0) Fischer dienyl carbenes 4a-4g with different terminal alkynes 3a-3l. Carbenes 4a-4g were pre-

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confidence: 86%

Regioselective Multicomponent Synthesis of 2,4,6‐Trisubstituted Phenols from Fischer Alkynyl Carbene Complexes

et al. 2016

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“…Once explored the reactivity of norbornene in the PKR, we tackled the PKR of dissymmetric fluorinated alkynes with ethylene [2], tetramethylnorbornadiene [22], and ( E )-cyclooctene [23], all of them used as alkenes in the PKR. As for the PKR with norbornene and in order to cover a representative range of electronic properties, we selected the same alkynes 1a – c as before.…”

Section: Resultsmentioning

confidence: 99%

“…In all cases only one PK adduct could be recovered upon purification and, after careful NMR analysis, all of them were assigned as the α-trifluoromethylcyclopentenones. Unfortunately, the reactions with other olefins were unsuccessful; complex 2d showed no reactivity with tetramethylnorbornadiene [22] after 24 h at 80 °C, whereas complex 2c decomposed in the presence of ( E )-cyclooctene [23] and NMO in methylene chloride.…”

Section: Resultsmentioning

confidence: 99%

Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity

et al. 2014

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Abstract:The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene.

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“…Most probably the α,β‐unsaturated ketone 5a was formed through dehydration of the corresponding hydroxyl ketone 3 . The unsaturated ketone 5a was previously reported as an advanced intermediate in the synthesis of a range of bioactive compounds and prostaglandin derivatives, thus allowing the unambiguous assignment of the absolute stereochemistry of the Heck products 6–8,10c,14…”

Section: Methodsmentioning

confidence: 99%

From Antidiabetic to Antifungal: Discovery of Highly Potent Triazole–Thiazolidinedione Hybrids as Novel Antifungal Agents

Zhang

et al. 2014

ChemMedChem

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In an attempt to discover a new generation of triazole antifungal agents, a series of triazole-thiazolidinedione hybrids were designed and synthesized by molecular hybridization of the antifungal agent fluconazole and rosiglitazone (an antidiabetic). Most of the target compounds showed good to excellent inhibitory activity against a variety of clinically important fungal pathogens. In particular, compounds (Z)-5-(2,4-dichlorobenzylidene)-3-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)thiazolidine-2,4-dione) (15 c), (Z)-3-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-5-(furan-3-ylmethylene)thiazolidine-2,4-dione (15 j), and (Z)-3-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-5-(furan-3-ylmethylene)thiazolidine-2,4-dione (15 r) were highly active against Candida albicans, with MIC80 values in the range of 0.03-0.15 μM. Moreover, compounds 15 j and 15 r were found to be effective against four fluconazole-resistant clinical isolates; these two compounds are particularly promising antifungal leads for further optimization. Molecular docking studies revealed that the hydrogen bonding interactions between thiazolidinedione and CYP51 from C. albicans are important for antifungal activity. This study also demonstrates the effectiveness of molecular hybridization in antifungal drug discovery.

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Tetramethylnorbornadiene, a Versatile Alkene for Cyclopentenone Synthesis through Intermolecular Pauson–Khand Reactions

Cited by 25 publications

References 31 publications

Regioselective Multicomponent Synthesis of 2,4,6‐Trisubstituted Phenols from Fischer Alkynyl Carbene Complexes

Regioselective Multicomponent Synthesis of 2,4,6‐Trisubstituted Phenols from Fischer Alkynyl Carbene Complexes

Pauson-Khand Reaction of Internal Dissymmetric Trifluoromethyl Alkynes. Influence of the Alkene on the Regioselectivity

From Antidiabetic to Antifungal: Discovery of Highly Potent Triazole–Thiazolidinedione Hybrids as Novel Antifungal Agents

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