Tandem Achmatowicz-Knoevenagel protocol: diastereoselective synthesis and anticancer evaluation of cyclopenta[b]pyrane derivatives.

Synthesis of cyclopenta[b]pyrane derivatives via Achmatowicz oxidative cyclization of furanols followed by intramolecular Knoevenagel condensation of the β-ketoester arm is examined. The extent of diastereoselectivity was dependent on the nature of the chiral atom within the tethering carbon of the pyrenone ring. In some cases, this process proceeds with a high degree of stereoselectivity after protection of the anomeric hydroxyl group. Furthermore, the cytotoxic activity of pyrazolone derivatives thereof was studied against HCT116 (human colorectal cancer cells), SK-N-SH (human Caucasian bone marrow neuroblastoma) cells and the non-tumorigenic cells (MCF10A).

[1]  Raed A. Al‐Qawasmeh,et al.  Synthesis and antimicrobial activity of cholic acid hydrazone analogues. , 2010, European journal of medicinal chemistry.

[2]  Raed A. Al‐Qawasmeh,et al.  Rational design and synthesis of potent dibenzazepine motifs as beta-secretase inhibitors. , 2009, Journal of medicinal chemistry.

[3]  C. Afonso,et al.  Synthesis of cyclopentitols by ring-closing approaches. , 2009, Chemical reviews.

[4]  Raed A. Al‐Qawasmeh,et al.  Differential use of anhydropyranosides for enantiopure routes to bis-gamma-butyrolactones: a new approach to the frameworks of antibiotic and anticancer agents isoavenaciolide and ethisolide. , 2009, The Journal of organic chemistry.

[5]  M. Krische,et al.  Asymmetric total synthesis of the iridoid beta-glucoside (+)-geniposide via phosphine organocatalysis. , 2009, Organic letters.

[6]  E. De Clercq,et al.  Mutations in the Nonstructural Protein 3A Confer Resistance to the Novel Enterovirus Replication Inhibitor TTP-8307 , 2009, Antimicrobial Agents and Chemotherapy.

[7]  G. O'Doherty,et al.  De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide. , 2008, The Journal of organic chemistry.

[8]  J. Taira,et al.  Cytotoxic Metabolites from the Okinawan Ascidian Diplosoma virens , 2008, Molecules.

[9]  G. O'Doherty,et al.  De novo asymmetric synthesis of 8a-epi-swainsonine. , 2008, The Journal of organic chemistry.

[10]  G. O'Doherty,et al.  De Novo Asymmetric Syntheses of d-, l- and 8-epi-Swainsonine. , 2008, Tetrahedron.

[11]  P. Krishna,et al.  Studies directed towards the stereoselective total synthesis of ilexlactone via a tandem ring-closing enyne metathesis protocol , 2007 .

[12]  G. O'Doherty,et al.  De novo asymmetric synthesis of the anthrax tetrasaccharide by a palladium-catalyzed glycosylation reaction. , 2007, Angewandte Chemie.

[13]  Rai‐Shung Liu,et al.  Dicobaltoctacarbonyl-mediated synthesis of tricyclic 5,6-diydropyran-2-one derivatives via tandem cycloaddition reaction between cis-epoxyalkynes, a tethered olefin, and carbon monoxide. , 2007, The Journal of organic chemistry.

[14]  A. Padwa,et al.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family. , 2006, The Journal of organic chemistry.

[15]  H. Hilal,et al.  Synthesis of a new series of heterocyclic scaffolds for medicinal purposes. , 2006, European journal of medicinal chemistry.

[16]  G. O'Doherty,et al.  De novo asymmetric synthesis of D- and L-swainsonine. , 2006, Organic letters.

[17]  P. Venturello,et al.  New synthetic approach to cyclopenta-fused heterocycles based upon a mild nazarov reaction. 2. Further studies on the torquoselectivity. , 2004, The Journal of organic chemistry.

[18]  Stuart L Schreiber,et al.  A synthesis strategy yielding skeletally diverse small molecules combinatorially. , 2004, Journal of the American Chemical Society.

[19]  D. Trauner,et al.  Enantioselective Nazarov reactions through catalytic asymmetric proton transfer. , 2004, Journal of the American Chemical Society.

[20]  U. Jahn,et al.  Efficient oxidative radical cyclizations of ester enolates with carbocation desilylation as termination: synthesis of cyclopentanoid monoterpenes and analogues. , 2004, Organic letters.

[21]  P. Venturello,et al.  New synthetic approach to cyclopenta-fused heterocycles based upon a mild Nazarov reaction. , 2003, The Journal of organic chemistry.

[22]  E. Jacobsen,et al.  Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereoselective synthesis of iridoid natural products. , 2003, Organic letters.

[23]  J. Mascareñas,et al.  Synthesis of fused oxabicyclic systems by metal-catalyzed intramolecular addition of 1,3-cycloalkyldiones to alkynes. , 2003, Organic letters.

[24]  F. J. Fañanás,et al.  Solvent-controlled diastereoselective synthesis of cyclopentane derivatives by a [3 + 2] cyclization reaction of alpha,beta-disubstituted (alkenyl)(methoxy)carbene complexes with methyl ketone lithium enolates. , 2003, Journal of the American Chemical Society.

[25]  M. Bradley,et al.  Solid-phase Friedel–Crafts acylation on polystyrene resins-synthesis of antiepiletic 1-aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones , 2001 .

[26]  G. Zanoni,et al.  Enantioselective synthesis of cis-1,2-dialkyl substituted cyclopentanoid and isoprostane building blocks via 6-exo-trigonal radical cyclizations , 2001 .

[27]  Jingbo Yan,et al.  Relative Asymmetric Induction in the Intramolecular Reaction between Alkynes and Cyclopropylcarbene−Chromium Complexes: Stereocontrolled Synthesis of Five-Membered Rings Fused to Oxygen Heterocycles , 1999 .

[28]  S. Hegde,et al.  Synthesis of 1,6-dihydro-5-hydroxy-6-oxo-3-(trifluoromethyl)-4-pyridazinecarboxylates , 1993 .

[29]  H. Ammon,et al.  A general approach to the stereoselective synthesis of spiroketals. A total synthesis of the pheromones of the olive fruit fly and related compounds , 1988 .

[30]  S. Martin,et al.  A stereoselective synthesis of (+)-Prelog-Djerassi lactone from furanoid intermediates , 1987 .

[31]  L. Humber,et al.  Cycloalkanoindoles. 1. Syntheses and antiinflammatory actions of some acidic tetrahydrocarbazoles, cyclopentindoles, and cycloheptindoles. , 1976, Journal of medicinal chemistry.

[32]  G. O'Doherty,et al.  The de novo synthesis of oligosaccharides: application to the medicinal chemistry SAR-study of digitoxin. , 2008, Current topics in medicinal chemistry.

[33]  K. Prasad,et al.  A general and facile synthesis of 1,3‐diaryl‐4‐pyrazoleacetic acid esters , 2005 .

[34]  D. M. Morgan,et al.  Tetrazolium (MTT) assay for cellular viability and activity. , 1998, Methods in molecular biology.

[35]  Y. Al-Abed,et al.  PALLADIUM-COBALT-MEDIATED DOUBLE ANNULATION PROCESS : A NEW STRATEGY TO CHIRAL AND POLYSUBSTITUTED BIS-CYCLOPENTANOIDS ON CARBOHYDRATE PRECURSORS , 1996 .

[36]  T. Al‐Tel,et al.  EFFICIENT ACCESS TO POLYFUNCTIONALIZED AND POLYCYCLIC FURANOIDS : CONTROL OF THE OFF-TEMPLATE CENTRE VIA ACID CATALYSIS , 1995 .

[37]  G. Spalluto,et al.  Nitrile Oxide [3 + 2] Cycloaddition: Application to the Synthesis of 6-Substituted 3(2H)-Pyridazinones and 6-Substituted 4,5-Dihydro-4-hydroxy-3(2H)-pyridazinones , 1994 .

[38]  Y. Al-Abed,et al.  A facile approach to polysubstituted chiral dihydrofurans on carbohydrate templates , 1994 .

[39]  I. Mackay,et al.  Validation of the MTT dye assay for enumeration of cells in proliferative and antiproliferative assays. , 1992, Biochemistry international.

[40]  P. DeShong,et al.  Acid-catalyzed rearrangement of pyran derivatives. An approach to the stereoselective synthesis of 1,3-diol derivatives , 1989 .

[41]  H. Budzikiewicz,et al.  Ilex-lacton, ein bisnormonoterpen neuartiger struktur aus Ilex aquifolium , 1980 .

[42]  D. Faulkner,et al.  Antimicrobial metabolites from the marine sponge ulosa sp. , 1978 .

[43]  O. Achmatowicz,et al.  Synthesis of methyl 2,3-dideoxy-DL-alk-2-enopyranosides from furan compounds , 1971 .