Synthèse racémique et énantiosélective d’énol-lactones et leur évaluation comme inhibiteurs de la protéase du VIH-1

Ibrahimi, Sanae; Sauvé, Gilles; Yelle, Joslyn; Essassi, El Mokhtar

doi:10.1016/j.crci.2004.08.002

Cited by 4 publications

(2 citation statements)

References 21 publications

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“…[3] Prepared following the procedure B and purified by column chromatography using EtOAc/hexane and isolated as 3-Benzyl-4-hydroxy-6-methyl-pyran-2-one (7ca): [4] Prepared following the procedure A and purified by column chromatography using EtOAc/hexane and isolated as a solid. 3-Benzyl-4-hydroxy-6-phenyl-5,6-dihydro-pyran-2-one (7da): [5] Prepared following the procedure A and purified by column chromatography using…”

Section: -Hydroxy-3-naphthalen-1-ylmethyl-5h-furan-2-one (7ab)mentioning

confidence: 99%

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Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions

Ramachary

Kishor

2010

Org. Biomol. Chem.

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A practical and sustainable chemical process for the synthesis of highly substituted tetrahydro-isobenzofuran-1,5-diones was achieved for the first time through asymmetric cascade Michael-aldol reaction of 4-hydroxy-3-alkyl-5H-furan-2-ones with alkyl vinyl ketones in the presence of a catalytic amount of l-proline or 9-amino-9-deoxyepiquinine/TCA. In this article, we discovered for the first time the asymmetric synthesis of privileged bicyclic lactones through kinetic resolution and show the synthetic application to pharmaceuticals and natural products synthesis.

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Section: -Hydroxy-3-naphthalen-1-ylmethyl-5h-furan-2-one (7ab)mentioning

confidence: 99%

“…Mp. : 4-Hydroxy-6-phenyl-3-(4-trifluoromethyl-benzyl)-5,6-dihydro-pyran-2-one (7dk): [5] Prepared following the procedure A and purified by column chromatography using EtOAc/hexane and isolated as a solid. Mp.…”

Section: -Hydroxy-3-(4-methyl-benzyl)mentioning

confidence: 99%

Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions

Ramachary

Kishor

2010

Org. Biomol. Chem.

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Recent Advances in the Field of Naturally Occurring 5,6‐Dihydropyran‐2‐ones

Marco

Cardá

2013

Natural Lactones and Lactams

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Palladium NNC Pincer Complex as an Efficient Catalyst for the Cycloisomerization of Alkynoic Acids

et al. 2016

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At wo-step( nucleophilic substitution/palladation by oxidative addition) sequence provides ah igh-yielding access to an on-symmetrical palladium NNC pincerc omplex. An umber of terminal and internal alkynoic acids with different substitution patternsa tt he a-a nd b-positions are regioand diastereoselectively cycloisomerizedt ot he corresponding exocyclic enol lactones in the presence of exceedingly low amounts of the latter palladium complex, so that unprecedented turnovern umbers and frequencies ranging from 1,000,000 to 700,000 and from 41,667 to 9722h À1 ,r espectively, are achieved. Theo ptimized protocol, based on the use of ac atalytic amount of triethylamine as base,a llows an easy real-time monitoring of the reactionb y NMR spectroscopy.S everal pieces of evidence in favor of the direct participation of the above pincer complex as the catalyst of the reaction have been gathered from kinetic and poisoning experiments

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Synthèse racémique et énantiosélective d’énol-lactones et leur évaluation comme inhibiteurs de la protéase du VIH-1

Cited by 4 publications

References 21 publications

Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions

Direct catalytic asymmetric synthesis of highly functionalized tetronic acids/tetrahydro-isobenzofuran-1,5-diones via combination of cascade three-component reductive alkylations and Michael-aldol reactions

Recent Advances in the Field of Naturally Occurring 5,6‐Dihydropyran‐2‐ones

Palladium NNC Pincer Complex as an Efficient Catalyst for the Cycloisomerization of Alkynoic Acids

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