The Piancatelli rearrangement of non-symmetrical furan-2,5-dicarbinols for the synthesis of highly functionalized cyclopentenones

Piancatelli rearrangement on substituted non-symmetrical furan-2,5-dicarbinols has been developed using an effective combination of microwave activation and Lewis acid catalyst.

[1]  V. Gandon,et al.  Aza‐Piancatelli Cyclization as a Platform for the Preparation of Scaffolds of Natural Compounds: Application to the Total Synthesis of Bruceolline D , 2020 .

[2]  F. Popowycz,et al.  5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals. , 2019, Current organic synthesis.

[3]  S. Royer,et al.  How Catalysts and Experimental Conditions Determine the Selective Hydroconversion of Furfural and 5-Hydroxymethylfurfural. , 2018, Chemical reviews.

[4]  F. Popowycz,et al.  The Piancatelli reaction and its variants: recent applications to high added-value chemicals and biomass valorization. , 2018, Organic & biomolecular chemistry.

[5]  Xing-Long Li,et al.  Effect of Cp*Iridium(III) Complex and acid co-catalyst on conversion of furfural compounds to cyclopentanones or straight chain ketones , 2017 .

[6]  A. Satsuma,et al.  Hydrogenative ring-rearrangement of biomass derived 5-(hydroxymethyl)furfural to 3-(hydroxymethyl)cyclopentanol using combination catalyst systems of Pt/SiO2 and lanthanoid oxides , 2017 .

[7]  J. Ouazzani,et al.  Total synthesis of the antibiotic 4-hydroxycyclopent-2-en-1-one acrylate derivative EA-2801 , 2017 .

[8]  M. Zanella,et al.  Selective conversion of 5-hydroxymethylfurfural to cyclopentanone derivatives over Cu–Al2O3 and Co–Al2O3 catalysts in water , 2017 .

[9]  Huaping Xu,et al.  Catalyst-Controlled Chemodivergent Modification of Indoles with 2-Furylcarbinols: Piancatelli Reaction vs Cross-Dehydrative Coupling Reaction. , 2017, The Journal of organic chemistry.

[10]  Mingguo Ma,et al.  Advances in the conversion of glucose and cellulose to 5-hydroxymethylfurfural over heterogeneous catalysts , 2016 .

[11]  Tiefeng Wang,et al.  Furfural: A Promising Platform Compound for Sustainable Production of C4 and C5 Chemicals , 2016 .

[12]  L. Vares,et al.  Application of 5-Ethoxymethylfurfural (EMF) for the Production of Cyclopentenones , 2016, Synthesis.

[13]  M. Oba,et al.  Synthesis of chiral five‐membered carbocyclic ring amino acids with an acetal moiety and helical conformations of its homo‐chiral homopeptides , 2016, Biopolymers.

[14]  A. Satsuma,et al.  The effect of heterogeneous acid–base catalysis on conversion of 5-hydroxymethylfurfural into a cyclopentanone derivative , 2016 .

[15]  S. Gayathri,et al.  Facile synthesis of 5-hydroxymethylfurfural: a sustainable raw material for the synthesis of key intermediates toward 21,23-dioxaporphyrins , 2015 .

[16]  K. Kulig,et al.  Asymmetric synthesis of all four stereoisomers of 1-amino-3-hydroxy-cyclopentane-1-carboxylic acid , 2015 .

[17]  V. Gandon,et al.  Calcium(II)-catalyzed aza-Piancatelli reaction. , 2014, Organic letters.

[18]  David J. Fisher,et al.  Efficient synthesis of 4-hydroxycyclopentenones: dysprosium(III) triflate catalyzed Piancatelli rearrangement , 2014 .

[19]  G. Pattenden,et al.  The versatility of furfuryl alcohols and furanoxonium ions in synthesis. , 2014, Chemical communications.

[20]  A. Satsuma,et al.  Conversion of 5-hydroxymethylfurfural to a cyclopentanone derivative by ring rearrangement over supported Au nanoparticles. , 2014, Chemical communications.

[21]  B. Shanks,et al.  Catalytic dehydration of C6 carbohydrates for the production of hydroxymethylfurfural (HMF) as a versatile platform chemical , 2014 .

[22]  Xue-hui Li,et al.  Synthesis, Skeletal Rearrangement, and Biological Activities of Spirooxindoles: Exploration of a Stepwise C‐Piancatelli Rearrangement , 2014 .

[23]  J. R. D. Alaniz,et al.  Rapid synthesis of fused oxabicycles through the molecular rearrangement of spirocyclic ethers , 2013 .

[24]  C. Piutti,et al.  The Piancatelli Rearrangement: New Applications for an Intriguing Reaction , 2013, Molecules.

[25]  Tiejun Wang,et al.  High yield production of 5-hydroxymethylfurfural from cellulose by high concentration of sulfates in biphasic system , 2013 .

[26]  Ed de Jong,et al.  Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. , 2013, Chemical reviews.

[27]  R. Katsuta,et al.  Synthesis of the core framework of the proposed structure of sargafuran , 2013 .

[28]  Leoni I Palmer,et al.  Rapid and stereoselective synthesis of spirocyclic ethers via the intramolecular Piancatelli rearrangement. , 2013, Organic letters.

[29]  M. K. Harper,et al.  Investigations of the marine flora and fauna of the Fiji Islands. , 2012, Natural product reports.

[30]  Huanfeng Jiang,et al.  Cu(II)-promoted transformations of α-thienylcarbinols into spirothienooxindoles: regioselective halogenation of dienyl sulfethers containing electron-rich aryl rings. , 2012, The Journal of organic chemistry.

[31]  J. Malinowski,et al.  Diastereocontrolled construction of pactamycin's complex ureido triol functional array. , 2012, Organic letters.

[32]  C. Liaw,et al.  Asperjinone, a nor-neolignan, and terrein, a suppressor of ABCG2-expressing breast cancer cells, from thermophilic Aspergillus terreus. , 2012, Journal of natural products.

[33]  Huanfeng Jiang,et al.  A Novel Entry to Spirofurooxindoles Involving Tandem Dearomatization of Furan Ring and Intramolecular Friedel– Crafts Reaction , 2011 .

[34]  Leoni I Palmer,et al.  Direct and highly diastereoselective synthesis of azaspirocycles by a dysprosium(III) triflate catalyzed aza-Piancatelli rearrangement. , 2011, Angewandte Chemie.

[35]  C. Afonso,et al.  5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties, synthesis and synthetic applications , 2011 .

[36]  J. Read de Alaniz,et al.  Versatile method for the synthesis of 4-aminocyclopentenones: dysprosium(III) triflate catalyzed aza-piancatelli rearrangement. , 2010, Angewandte Chemie.

[37]  Xinli Tong,et al.  Biomass into chemicals: Conversion of sugars to furan derivatives by catalytic processes , 2010 .

[38]  Joseph J. Bozell,et al.  Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited , 2010 .

[39]  Biaolin Yin,et al.  Novel Conversions of Furandiols and Spiroacetal Enol Ethers into Cyclopentenones: Implications of the Isomerization Mechanism of 2‐Furylcarbinols into Cyclopentenones , 2009 .

[40]  R. Batey,et al.  Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process. , 2007, Chemical communications.

[41]  G. Ramana,et al.  Stereoselective approach to pentenocins using RCM: synthesis of 6-epi-pentenocin B , 2006 .

[42]  J. M. Sanderson,et al.  The synthesis of peptides and proteins containing non-natural amino acids. , 2004, Chemical Society reviews.

[43]  A. Kuboki,et al.  Synthesis and structure of diastereomers of pentenocin B produced by Trichoderma hamatum FO-6903 , 2004 .

[44]  E. Ghisalberti.  Anti-Infective Agents Produced by the Hyphomycetes Genera Trichoderma and Gliocladium , 2002 .

[45]  Biaolin Yin,et al.  Acid catalysed rearrangement of a spiroketal enol ether. An easy synthesis of chrycorin , 2002 .

[46]  A. Numata,et al.  First total syntheses and configurational assignments of cytotoxic trichodenones A–C , 2000 .

[47]  Hoffmann.  Conformation Design of Open-Chain Compounds. , 2000, Angewandte Chemie.

[48]  M. D’Auria.  A New Simple Procedure for the Isomerization of 2-Furylcarbinols to Cyclopentenones , 2000 .

[49]  S. Ōmura,et al.  Novel cyclopentanone derivatives pentenocins A and B with interleukin-1beta converting enzyme inhibitory activity, produced by Trichoderma hamatum FO-6903. , 1999, The Journal of antibiotics.

[50]  A. Numata,et al.  Total Syntheses of Trichodenones A-C , 1999 .

[51]  A. Siriwardena,et al.  Synthesis and Biological Activity of Natural Aminocyclopentitol Glycosidase Inhibitors: Mannostatins, Trehazolin, Allosamidins, and Their Analogues. , 1999, Chemical reviews.

[52]  A. Numata,et al.  Cytotoxic substances produced by a fungal strain from a sponge: physico-chemical properties and structures. , 1998, The Journal of antibiotics.

[53]  S. Takano,et al.  Total Syntheses of Didemnenones C and D , 1995 .

[54]  F. West,et al.  Pseudocine substitution via internal delivery. Formal cyclopentadienone-ketone Michael adducts from 4-hydroxycyclopentenones , 1993 .

[55]  J. Clardy,et al.  Isolation and structure determination of the didemnenones, novel cytotoxic metabolites from tunicates , 1988 .

[56]  G. Piancatelli,et al.  General route and mechanism of the rearrangement of the 4-substituted 5-hydroxy-3-oxocyclopentenes into the 2-substituted analogs , 1979 .

[57]  G. Piancatelli,et al.  A new synthesis of 3-oxocyclopentenes , 1978 .

[58]  G. Piancatelli,et al.  A useful preparation of 4-substituted 5-hydroxy-3-oxocyclopentene , 1976 .