Stereospecific novel glycosylation of hydroxy β-lactams via iodine-catalyzed reaction: a new method for optical resolution

[1]  R. Mohan,et al.  Applications of bismuth(III) compounds in organic synthesis. , 2003, Chemical Society reviews.

[2]  F. Becker,et al.  Novel Anticancer β-Lactams , 2011 .

[3]  A. Jarrahpour,et al.  Efficient one-pot synthesis of 2-azetidinones from acetic acid derivatives and imines using methoxymethylene-N,N-dimethyliminium salt , 2010 .

[4]  A. Slawin,et al.  Chiral relay in NHC-mediated asymmetric β-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine , 2010 .

[5]  F. Becker,et al.  Selective anticancer activity of β-lactams derived from polyaromatic compound. , 2010, Molecular medicine reports.

[6]  F. Becker,et al.  Asymmetric synthesis of anticancer β-lactams via Staudinger reaction. , 2010, Molecular medicine reports.

[7]  F. Becker,et al.  Asymmetric synthesis of anticancer beta-lactams via Staudinger reaction: utilization of chiral ketene from carbohydrate. , 2010, European journal of medicinal chemistry.

[8]  B. Basu,et al.  Recent Approaches Toward Solid Phase Synthesis of β-Lactams , 2010 .

[9]  Takao Saito,et al.  Enantioselective synthesis of β-lactams via the IndaBox–Cu(II)-catalyzed Kinugasa reaction , 2009 .

[10]  M. Shimizu,et al.  Stereodivergent synthesis of beta-lactams using thermal rearrangement of aminocyclobutenones. , 2009, Organic Letters.

[11]  S. Gellman,et al.  Synthesis of beta-lactams bearing functionalized side chains from a readily available precursor. , 2008, Organic letters.

[12]  S. Gürtler,et al.  β-Lactam derivatives as potential anti-cancer compounds , 2008 .

[13]  A. Slawin,et al.  N-Heterocyclic carbene catalysed beta-lactam synthesis. , 2008, Organic & biomolecular chemistry.

[14]  Andrew J. S. Knox,et al.  β-Lactam type molecular scaffolds for antiproliferative activity: Synthesis and cytotoxic effects in breast cancer cells , 2008 .

[15]  Matteo Dal Peraro,et al.  Role of zinc content on the catalytic efficiency of B1 metallo beta-lactamases. , 2007, Journal of the American Chemical Society.

[16]  F. Fülöp,et al.  Do lipases also catalyse the ring cleavage of inactivated cyclic trans-β-lactams? , 2006 .

[17]  B. Arndtsen,et al.  Direct, palladium-catalyzed, multicomponent synthesis of beta-lactams from imines, acid chloride, and carbon monoxide. , 2006, Organic letters.

[18]  Jian Zhou,et al.  Trisoxazoline/Cu(II)-promoted Kinugasa reaction. Enantioselective synthesis of beta-lactams. , 2006, The Journal of organic chemistry.

[19]  Elaine C. Lee,et al.  Catalytic asymmetric Staudinger reactions to form beta-lactams: an unanticipated dependence of diastereoselectivity on the choice of the nitrogen substituent. , 2005, Journal of the American Chemical Society.

[20]  F. Becker,et al.  Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction , 2005 .

[21]  S. Dasgupta,et al.  A straightforward highly efficient Paal–Knorr synthesis of pyrroles , 2005 .

[22]  B. Banik,et al.  Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition , 2005 .

[23]  B. Banik,et al.  A remarkable iodine-catalyzed protection of carbonyl compounds , 2005 .

[24]  Bin Wu,et al.  PdCl2-catalyzed efficient transformation of propargylic amines to (E)-α-chloroalkylidene-β-lactams , 2005 .

[25]  T. Lectka,et al.  Bifunctional Lewis acid-nucleophile-based asymmetric catalysis: mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of beta-lactams. , 2005, Journal of the American Chemical Society.

[26]  A. Porcheddu,et al.  A New Polymer-Supported Reagent for the Synthesis of β-Lactams in Solution , 2004 .

[27]  D. Burnett β-lactam cholesterol absorption inhibitors , 2004 .

[28]  J. Aizpurua,et al.  Asymmetric Synthesis of β-Lactams Through the Staudinger Reaction and Their Use as Building Blocks of Natural and Nonnatural Products , 2004 .

[29]  T. Lectka,et al.  Development of a new dimeric cyclophane ligand: application to enhanced diastereo- and enantioselectivity in the catalytic synthesis of beta-lactams. , 2004, Journal of Organic Chemistry.

[30]  F. Becker,et al.  Synthesis of anticancer β-lactams: mechanism of action , 2004 .

[31]  T. Lectka,et al.  Advances in the Catalytic, Asymmetric Synthesis of β-Lactams , 2004 .

[32]  G. C. Fu Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine. , 2004, Accounts of chemical research.

[33]  D. Kuhn,et al.  Novel N-thiolated beta-lactam antibiotics selectively induce apoptosis in human tumor and transformed, but not normal or nontransformed, cells. , 2004, Biochemical Pharmacology.

[34]  B. Banik,et al.  Simple synthesis of substituted pyrroles. , 2004, The Journal of organic chemistry.

[35]  B. Banik,et al.  A new bismuth nitrate-induced stereospecific glycosylation of alcohols , 2003 .

[36]  G. S. Singh Recent Progress in the Synthesis and Chemistry of Azetidinones , 2003 .

[37]  G. C. Fu,et al.  Catalytic enantioselective synthesis of beta-lactams: intramolecular Kinugasa reactions and interception of an intermediate in the reaction cascade. , 2003, Angewandte Chemie.

[38]  B. Banik,et al.  Cycloaddition of naphthalenyl and anthracenyl imines: Interesting aspects of the Staudinger reaction , 2003 .

[39]  B. Banik,et al.  Bismuth nitrate-catalyzed versatile Michael reactions. , 2003, The Journal of organic chemistry.

[40]  S. Dasgupta,et al.  A remarkable bismuth nitrate-catalyzed protection of carbonyl compounds , 2003 .

[41]  F. Becker,et al.  Stereoselective synthesis of beta-lactams with polyaromatic imines: entry to new and novel anticancer agents. , 2003, Journal of medicinal chemistry.

[42]  Thierry Ollevier,et al.  An efficient method for the ring opening of epoxides with aromatic amines catalyzed by bismuth trichloride , 2002 .

[43]  B. M. Choudary,et al.  Highly efficient allylation of aldehydes and three-component synthesis of homoallylamines using bismuth triflate catalyst , 2002 .

[44]  T. Toupance,et al.  Efficient bismuth catalysts for transcarbamoylation , 2002 .

[45]  B. Banik,et al.  MORE Chemistry for Less Pollution: Applications for Process Development , 2002 .

[46]  A. Das,et al.  An asymmetric synthesis of β-lactams: on the use of chiral oxazolidones in the Kinugasa reaction , 2002 .

[47]  R. Mohan,et al.  A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate. , 2002, The Journal of organic chemistry.

[48]  G. C. Fu,et al.  Cu(I)/bis(azaferrocene)-catalyzed enantioselective synthesis of beta-lactams via couplings of alkynes with nitrones. , 2002, Journal of the American Chemical Society.

[49]  Y. Venkateswarlu,et al.  An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement. , 2002 .

[50]  F. Tanaka,et al.  A Highly Enantioselective Route to Either Enantiomer of Both α- and β-Amino Acid Derivatives , 2002 .

[51]  N. Miyoshi,et al.  Bismuth Trichloride Catalyzed Efficient Reductive Etherification of Carbonyl Compounds with Alcohols : A Novel Method for Preparation of Symmetrical and Unsymmetrical Ethers , 2002 .

[52]  J. Dubac,et al.  Bismuth(III) Chloride and Triflate: Novel Catalysts for Acylation and Sulfonylation Reactions. Survey and Mechanistic Aspects , 2002 .

[53]  G. C. Fu,et al.  Enantioselective Staudinger synthesis of beta-lactams catalyzed by a planar-chiral nucleophile. , 2002, Journal of the American Chemical Society.

[54]  R. Mohan,et al.  A simple and efficient chemoselective method for the catalytic deprotection of acetals and ketals using bismuth triflate. , 2002, The Journal of organic chemistry.

[55]  J. Yadav,et al.  Bismuth(III) chloride: An efficient catalyst for the one-pot stereoselective synthesis of octahydroacridines , 2002 .

[56]  Plato A. Magriotis Neues über die enantioselektive Synthese vonβ-Lactamen: Entwicklung der ersten katalytischen Ansätze , 2001 .

[57]  J. Barrett,et al.  Quinolone, everninomycin, glycylcycline, carbapenem, lipopeptide and cephem antibacterials in clinical development. , 2001, Current Medicinal Chemistry.

[58]  J. Tierney,et al.  Microwave assisted organic synthesis-a review , 2001 .

[59]  A. Loupy,et al.  A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations , 2001 .

[60]  M. K. Basu,et al.  A new molecular iodine-catalyzed thioketalization of carbonyl compounds: selectivity and scope , 2001 .

[61]  J. Roque,et al.  Reactivity of bismuth(III) halides towards alcohols. A tentative to mechanistic investigation , 2001 .

[62]  J. Yadav,et al.  Bismuth (III) chloride-catalyzed intramolecular hetero diels-Alder reaction: application to the synthesis of tetrahydrochromano [4, 3-b] quinoline derivatives , 2001 .

[63]  J. Aizpurua,et al.  β-Lactams as Versatile Intermediates in α- and β-Amino Acid Synthesis , 2001 .

[64]  K. Ramalinga,et al.  Bismuth(III)-Catalyzed Synthesis of Dihydropyrimidinones: Improved Protocol Conditions for the Biginelli Reaction , 2001 .

[65]  M. Gómez-Gallego,et al.  Non-Classical Polycyclic β-Lactams , 2000 .

[66]  T. Lectka,et al.  Catalytic, Asymmetric Synthesis of β-Lactams , 2000 .

[67]  B. Banik,et al.  Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques , 2000 .

[68]  Ge Wu A Concise Asymmetric Synthesis of A β-Lactam-Based Cholesterol Absorption Inhibitor , 2000 .

[69]  M. Benaglia,et al.  The S-Thioester Enolate/Imine Condensation: A Shortcut to β-Lactams , 2000 .

[70]  J. Aizpurua,et al.  Asymmetric Synthesis of β‐Lactams by Staudinger Ketene‐Imine Cycloaddition Reaction , 1999 .

[71]  B. Banik,et al.  Microwave-Assisted Rapid and Simplified Hydrogenation1,† , 1999 .

[72]  N. Westwood,et al.  Mechanistic insights into the inhibition of serine proteases by monocyclic lactams. , 1999, Biochemistry.

[73]  L. Tarsi,et al.  The renewed challenge of antibacterial chemotherapy , 1998 .

[74]  B. Banik,et al.  Enantiopure α-hydroxy-β-lactams via stereoselective glycosylation , 1997 .

[75]  E. W. Robb,et al.  ENVIRONMENTALLY BENIGN CHEMISTRY : MICROWAVE-INDUCED STEREOCONTROLLED SYNTHESIS OF BETA -LACTAM SYNTHONS , 1997 .

[76]  B. Banik,et al.  ENANTIOMERICALLY PURE BETA -LACTAMS WITH THE THIENAMYCIN SIDE CHAIN VIA GLYCOSYLATION , 1997 .

[77]  J. Clader,et al.  Metabolism and structure activity data based drug design: discovery of (−) SCH 53079 an analog of the potent cholesterol absorption inhibitor (−) SCH 48461 , 1996 .

[78]  B. Fraser-Reid Some progeny of 2,3-unsaturated sugars - they little resemble grandfather glucose: ten years later , 1996 .

[79]  M. Chmielewski,et al.  Stereocontrolled synthesis of 1-oxabicyclic β-lactam antibiotics via[2 + 2]cycloaddition of isocyanates to sugar vinyl ethers , 1996 .

[80]  I. Ojima Recent Advances in the .beta.-Lactam Synthon Method , 1995 .

[81]  M. Miura,et al.  Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives , 1995 .

[82]  A. Maycock,et al.  Orally active beta-lactam inhibitors of human leukocyte elastase. 3. Stereospecific synthesis and structure-activity relationships for 3,3-dialkylazetidin-2-ones. , 1995, Journal of medicinal chemistry.

[83]  A. M. Gómez,et al.  Ferrier Rearrangement under Nonacidic Conditions Based on Iodonium-Induced Rearrangements of Allylic n-Pentenyl Esters, n-Pentenyl Glycosides, and Phenyl Thioglycosides , 1995 .

[84]  M. Nakata,et al.  Practical Glycosidation Method of Glycals Using Montmorillonite K-10 as an Environmentally Acceptable and Inexpensive Industrial Catalyst , 1995 .

[85]  C. Boschetti,et al.  β-Lactam Compounds. Inhibitors of Transpeptidases, β-Lactamases and Elastases: A Review , 1995, Current Medicinal Chemistry.

[86]  A. Spatola,et al.  Mechanism of Palladium-Catalyzed Transfer Hydrogenolysis of Aryl Chlorides by Formate Salts , 1995 .

[87]  Michael L. Shuler,et al.  Taxol®: science and applications. , 1995 .

[88]  E. W. Robb,et al.  Microwave-induced organic reaction enhancement (more) chemistry: Techniques for rapid, safe and inexpensive synthesis , 1994 .

[89]  R. Burrier,et al.  2-Azetidinones as inhibitors of cholesterol absorption. , 1994, Journal of medicinal chemistry.

[90]  P. Bernstein,et al.  Synthetic Inhibitors of Elastase , 1994, Medicinal research reviews.

[91]  R. Droghini,et al.  Synthesis of trans-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one. A key starting β-lactam for 2′-epi-taxol , 1993 .

[92]  A. Bose,et al.  Facile preparation of carbapenem synthons via microwave-induced rapid reaction , 1993 .

[93]  Jy Liu,et al.  A novel asymmetric synthesis of cis-3-hydroxy-4-aryl azetidin-2-ones , 1993 .

[94]  C. Swindell,et al.  Chiral auxiliary-mediated asymmetric induction in a thermal inverse electron demand hetero-Diels-Alder reaction. Enantioselective synthesis of the taxol A-ring side chain , 1993 .

[95]  K. Tatsuta,et al.  Recent progress in O-glycosylation methods and its application to natural products synthesis , 1993 .

[96]  J. Randolph,et al.  A strategy for the solid-phase synthesis of oligosaccharides. , 1993, Science.

[97]  S. Oberhoffner,et al.  Unexpected Formation of 3,6‐Anhydrofuranoses by Acid Treatment of Methyl 2,3‐Di‐O‐acyl‐D‐glycopyranosides , 1993 .

[98]  C. Sih,et al.  Chemoenzymic synthesis of the C-13 side chain of taxol: optically active 3-hydroxy-4-phenyl .beta.-lactam derivatives , 1993 .

[99]  Hisashi Yamamoto,et al.  Highly selective and operationally simple synthesis of enantiomerically pure .beta.-amino esters via double stereodifferentiation , 1993 .

[100]  B. Banik,et al.  Studies on lactams. 89. Versatile .beta.-lactam synthons: enantiospecific synthesis of (-)-polyoxamic acid , 1993 .

[101]  M. Nakata,et al.  Glycosidation of glycals by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a catalytic promoter , 1993 .

[102]  A. Kanazawa,et al.  A short synthesis of the taxotere side chain through dilithiation of boc-benzylamine , 1993 .

[103]  B. Banik,et al.  Simplified Rapid Hydrogenation Under Microwave Irradiation: Selective Transformations of β-Lactams1 , 1993 .

[104]  G. Georg,et al.  The Organic chemistry of β-lactams , 1993 .

[105]  M. R. Mejillano,et al.  Synthesis of biologically active taxol analogues with modified phenylisoserine side chains. , 1992, Journal of medicinal chemistry.

[106]  B. Banik,et al.  Microwave-induced organic reaction enhancement chemistry.4 convenient synthesis of enantiopure α-hydroxy-β-lactams1 , 1992 .

[107]  S. S. Bari,et al.  Stereoregulated synthesis of β-lactams from schiff bases derived from threonine esters , 1992 .

[108]  J. López,et al.  n-Pentenyl esters facilitate an oxidative alternative to the Ferrier rearrangement. An expeditious route to sucrose , 1992 .

[109]  I. Ojima,et al.  New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method , 1992 .

[110]  G. Koten,et al.  Syntheses of 3-amino-2-azetidinones: A literature survey , 1991 .

[111]  D. W. Balogh,et al.  An asymmetric synthesis of a 3-hydroxy-β-lactam by ketene-imine cycloaddition: utilization of chiral ketenes from carbohydrates , 1991 .

[112]  E. Bandini,et al.  Metallo-imines: Useful reagents in organic synthesis , 1990 .

[113]  J. Herscovici,et al.  C-Glycoside synthesis via glycal alkylation by olefinic derivatives , 1990 .

[114]  D. Hart,et al.  The ester enolate-imine condensation route to .beta.-lactams , 1989 .

[115]  S. Ram,et al.  Ammonium Formate in Organic Synthesis: A Versatile Agent in Catalytic Hydrogen Transfer Reductions , 1988 .

[116]  L. A. Carpino,et al.  The ((.beta.-phenylethyl)oxy)carbonyl ("homobenzyloxycarbonyl", hZ) amino-protecting group , 1986 .

[117]  R. R. Schmidt Neue Methoden zur Glycosid‐ und Oligosaccharidsynthese – gibt es Alternativen zur Koenigs‐Knorr‐Methode? , 1986 .

[118]  Marvin J Miller Hydroxamate approach to the synthesis of .beta.-lactam antibiotics , 1986 .

[119]  C. Hubschwerlen A convenient synthesis of L-(S)-glyceraldehyde acetonide from L-ascorbic acid , 1986 .

[120]  D. Horton,et al.  Allylic rearrangement of 6-deoxyglycals having practical utility. , 1985, Carbohydrate research.

[121]  B. Fraser-Reid Some Progeny of 2,3-Unsaturated SugarsThey Little Resemble Grandfather Glucose: Twenty Years Later†,1 , 1985 .

[122]  L. Overman,et al.  Total Synthesis of (−)-Crinine. Use of Tandem Cationic Aza-Cope Rearrangement/Mannich Cyclizations for the Synthesis of Enantiomerically Pure Amaryllidaceae Alkaloids†‡ , 1985 .

[123]  S. S. Bari,et al.  Enantiospecific synthesis of β-lactams via cycloaddition , 1985 .

[124]  G. Schmid,et al.  An enantioselective β-lactam synthesis starting from L-(S)-glyceraldehyde acetonide , 1983 .

[125]  A. Sartorelli,et al.  Cation-Exchange resin-catalyzed addition of methanol to benzoylated 1,5-anhydro-2-deoxy-d-hex-1-enitols , 1982 .

[126]  OjimaIwao,et al.  A NEW AND CONVENIENT ROUTE TO THE AMIDES OF α-AMINO ACIDS AND α-HYDROXY ACIDS BY MEANS OF THE PALLADIUM CATALYZED FACILE CLEAVAGE OF 3-SUBSTITUTED-4-ARYLAZETIDIN-2-ONES , 1980 .

[127]  A. Spatola,et al.  An Advantageous Method for the Rapid Removal of Hydrogenolysable Protecting Groups under Ambient Conditions; Synthesis of Leucine-enkephalin , 1980 .

[128]  W. Priebe,et al.  Synthesis of alkyl 4,6-di-o-acetyl-2,3-dideoxy-α-d-threo-hex-2- enopyranosides from 3,4,6-tri-o-acetyl-1,5-anhydro-2-deoxy- d-lyxo-hex-1-enitol (3,4,6-tri-o-acetyl-d-galactal) , 1979 .

[129]  J. Thiem,et al.  Synthese α-verknüpfter 2′-Deoxy-2′-iododisaccharide , 1978 .

[130]  Jean-Claude Martin,et al.  Sur l'isomérisation du 1,5-anhydro-3,4,6-tri-O-benzyl-1,2-didésoxy-d-arabino-hex-1-énitol on présence d'acides de Lewis , 1977 .

[131]  B. Fraser-Reid Progeny of 2,3-unsaturated sugars. They little resemble Grandfather Glucose , 1975 .

[132]  S. Hashimoto,et al.  The reactions of copper(I) phenylacetylide with nitrones , 1972 .

[133]  N. A. Sörensen,et al.  Preparation of Tri-O-benzoyl-2-deoxy-alpha-D-ribo-hexopyranosyl Fluoride from Derivatives of D-Glucal and Anhydrous Hydrogen Fluoride. , 1970 .

[134]  R. Ferrier,et al.  Unsaturated carbohydrates. Part IX. Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal , 1969 .

[135]  R. Lemieux,et al.  SUBSTITUTIONAL AND CONFIGURATIONAL EFFECTS ON CHEMICAL SHIFT IN PYRANOID CARBOHYDRATE DERIVATIVES , 1965 .

[136]  R. Ferrier 1038. Unsaturated carbohydrates. Part II. Three reactions leading to unsaturated glycopyranosides , 1964 .

[137]  H. Staudinger Zur Kenntniss der Ketene. Diphenylketen , 1907 .