The synthesis of natural β-lactam antibiotics

[1]  S. J. Reynolds,et al.  Synthesis of (±)-thienamycin based on a new approach to β-lactams via 4-exo-trig cyclisation of carbamoylcobalt salophens , 1994 .

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

[3]  James D White,et al.  A photochemical route to carbapenems from pyrazolidin-3-ones. Formal synthesis of PS-5 , 1993 .

[4]  O. Miyata,et al.  A novel stereoselective route to β-lactams : diastereoselective synthesis of a key intermediate for carbapenem antibiotic (+)-PS-5 , 1993 .

[5]  K. Koga,et al.  Stereoselective Reactions. XX. Synthetic Studies on Optically Active β-Lactams. III. Stereocontrolled Synthesis of Chiral Intermediate to (+)-Thienamycin from D-Glucose , 1991 .

[6]  A. Kaura,et al.  A convenient large scale synthesis of 7α-formamido cephalosporins , 1991 .

[7]  S. Hanessian,et al.  A novel ring-closure strategy for the carbapenems: the total synthesis of (+)-thienamycin , 1990 .

[8]  C. Townsend,et al.  Total syntheses of (−)-nocardicins A−G: a biogenetic approach , 1990 .

[9]  R. Southgate,et al.  Olivanic acid analogues. Part 6. Biomimetic synthesis of (±)-PS-5, (±)-6-Epi-PS-5, and (±)-benzyl MM22381 , 1990 .

[10]  Y. Sugimura,et al.  Synthetic studies of 1-beta-methylcarbapenem antibiotics. , 1989, The Journal of antibiotics.

[11]  T. Kawabata,et al.  Novel syntheses of the carbapenem key intermediates, (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone and (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone, from (S)-ethyl lactate , 1989 .

[12]  M. J. Pearson,et al.  Synthesis of novel 3-formamido-3-acylamino-monobactams , 1989 .

[13]  T. Shono,et al.  Diastereoselectivity in the addition of enolate anions to N-methoxycarbonylimines generated in situ from α-methoxy carbamates , 1989 .

[14]  T. Honda,et al.  Efficient chiral synthesis of Melillo's lactone, a key intermediate for the synthesis of thienamycin , 1989 .

[15]  R. Southgate,et al.  Recent advances in the chemistry of β-lactam antibiotics , 1989 .

[16]  D. Giacomini,et al.  .beta.-Lactams from ester enolates and silylimines. Enantioselective synthesis of (+)-PS-5 , 1988 .

[17]  R. Volante,et al.  An efficient synthesis of 4-benzoyloxyazetidinone: an important carbapenem intermediate , 1988 .

[18]  M. J. Pearson,et al.  Direct incorporation of a 6α(7α)-formamido group into penicillin and cephalosporin sulphides and sulphoxides , 1988 .

[19]  J. Odriozola,et al.  A short formal synthesis of the carbapenem antibiotic (±)-PS-5 , 1988 .

[20]  C. Gennari,et al.  TiCl4-mediated reactions of silyl ketene acetals derived from n-methylephedrine esters:asymmetric synthesis ofβ-lactams , 1988 .

[21]  T. Nakai,et al.  A new approach to the chiral synthesis of the 1-.beta.-methylcarbapenem key precursor using an achiral ketone Sn(II) enolate , 1987 .

[22]  Y. Ishida,et al.  Asymmetric synthesis of the carbapenem antibiotic (+)-PS-5 , 1987 .

[23]  T. Kametani,et al.  Enantioselective Syntheses of Carbapenem Antibiotics , 1987 .

[24]  Tohru Yamada,et al.  The Asymmetric Addition of the Sn(II) Enolates of Thioesters to α-Iminoesters. A Convenient Synthesis of Optically Active cis-Substituted β-Lactams. , 1987 .

[25]  G. Georg,et al.  Asymmetric synthesis of (1′R,3R,4R)-4-acetoxy-3-(1′-((tert-butyldimethylsilyl)oxy)ethyl)-2- azetidinone and other 3-(1′-Hydroxyethyl)-2-azetidinones from (S)-(+)-Ethyl 3-hydroxybutanoate: Formal total synthesis of (+)-thienamycin , 1987 .

[26]  T. Sowin,et al.  An efficient enantioselective synthesis of the carbapenam-2-one system. An approach to (+)-thienamycin and related carbapenems , 1987 .

[27]  M. J. Pearson,et al.  Preparation and properties of 7α-formamido cephalosporins , 1987 .

[28]  G. Burton,et al.  Studies on 6 alpha-substituted penicillins. II. Synthesis and structure-activity relationships of 6 beta-(2-aryl-2-sulfoacetamido)-6 alpha-methoxy penicillanic acids. , 1986, The Journal of antibiotics.

[29]  D. Hart,et al.  Asymmetric synthesis of .beta.-lactams and the carbapenem antibiotic (+)-PS-5. , 1986, Journal of the American Chemical Society.

[30]  J. Buynak,et al.  .alpha.-Akylidene .beta.-lactams. 2. A formal synthesis of (.+-.)-carpetimycin A , 1986 .

[31]  D. Melillo,et al.  An Enantioselective Approach to (+)-Thienamycin from Dimethyl 1,3-Acetonedicarboxylate and (+)-α -Methylbenzylamine. , 1986 .

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

[33]  R. Déziel,et al.  Simple and highly diastereoselective synthesis of a 1β-methylcarbapenem key intermediate involving divalent tin enolates , 1986 .

[34]  Davidr . Evans,et al.  The asymmetric synthesis of β-lactam antibiotics - III. Enantioselective synthesis of (+) PS-5 , 1986 .

[35]  R. Southgate,et al.  A stereocontrolled route to optically active 1-methyl carbapenems , 1986 .

[36]  S. Hanessian,et al.  Design and reactivity of organic functional groups—utility of imidazolylsulfonates in the synthesis of monobactams and 3-amino nocardicinic acid , 1985 .

[37]  S. Chu,et al.  Useful chemistry of 3-(1-methylethylidene)-4-acetoxy-2-azetidinones: a formal synthesis of (.+-.)-asparenomycin C , 1985 .

[38]  H. Maruyama,et al.  A Synthesis of a Versatile Intermediate Leading to Thienamycin Analogs , 1985 .

[39]  T. Yoshida,et al.  Carbapenem and penem antibiotics. I. Total synthesis and antibacterial activity of dl-asparenomycins A, B and C and related carbapenem antibiotics. , 1985, Chemical & pharmaceutical bulletin.

[40]  S. Tsubotani,et al.  Formadicins, new monocyclic beta-lactam antibiotics of bacterial origin. II. Isolation, characterization and structures. , 1985, The Journal of antibiotics.

[41]  T. Honda,et al.  Chiral synthesis of the key intermediates of (+)- and (−)-thienamycin , 1985 .

[42]  G. Burton,et al.  Preparation and structure-activity relationships of some 6 alpha-substituted penicillins. , 1985, The Journal of antibiotics.

[43]  Y. Ishida,et al.  A novel synthesis of (-)-carpetimycin A , 1985 .

[44]  M. J. Pearson,et al.  6α-Methylsulphinyl penicillins: useful intermediates for the introduction of 6α-substituents into penicillins , 1985 .

[45]  S. Ley,et al.  Synthesis of the β-lactam antibiotic (+)- thienamycin via an intermediate π-allyltricarbonyliron lactone complex , 1985 .

[46]  M. Hashimoto,et al.  Synthetic studies on carbapenem antibiotics from penicillins. III. Stereoselective radical reduction of a chiral 3-isocyanoazetidinone: a total synthesis of optically active carpetimycins2 , 1985 .

[47]  R. Southgate,et al.  Naturally occurring beta-lactams. , 1985, Fortschritte der Chemie organischer Naturstoffe = Progress in the chemistry of organic natural products. Progres dans la chimie des substances organiques naturelles.

[48]  T. C. Smale,et al.  6α(7α)-Formamido penicillins and cephalosporins , 1985 .

[49]  Y. Ueda,et al.  A simple method of preparing trimethylsilyl- and tert-butyldimethylsilyl-enol ethers of α-diazoacetoacetates and their use in the synthesis of a chiral precursor to thienamycin analogs , 1984 .

[50]  S. Tsubotani,et al.  Cephabacins, new cephem antibiotics of bacterial origin. III. Structural determination. , 1984, The Journal of antibiotics.

[51]  T. Kato,et al.  Chitinovorins A, B and C, novel beta-lactam antibiotics of bacterial origin. , 1984, The Journal of antibiotics.

[52]  S. Uyeo,et al.  Total synthesis of dl-asparenomycins A, B and C, novel carbapenem antibiotics , 1984 .

[53]  M. Young,et al.  Bacterial production of 7-formamidocephalosporins. Isolation and structure determination. , 1984, The Journal of antibiotics.

[54]  T. C. Smale.  A chiral intermediate for thienamycin analogue synthesis: (,)-4-(2-hydroxyethyl)-3-[()-1-(4-nitrobenzyloxycarbonyloxy)etryl]azetidin-2-one , 1984 .

[55]  M. Ohno,et al.  Stereocontrolled synthesis of an ene-carbapenem antibiotic (-)-asparenomycin C , 1983 .

[56]  H. Natsugari,et al.  Synthesis of 5,6-cis-carbapenems related to C-19393 H2 , 1983 .

[57]  M. Ohno,et al.  Stereocontrolled synthesis of a cis-carbapenem antibiotic (-)-carpetimycin A , 1983 .

[58]  D. Floyd,et al.  4-Alkylated monobactams : Chiral synthesis and antibacterial activity , 1983 .

[59]  H. Maruyama,et al.  Stereocontrolled syntheses of chiral and racemic key intermediates to thienamycin from d-allo-threonine and trans-crotonic acid , 1983 .

[60]  M. Miyashita,et al.  Synthesis of the precursor of (+)-thienamycin utilizing D-glucosamine , 1983 .

[61]  P. Reider,et al.  Total synthesis of thienamycin: a new approach from aspartic acid , 1982 .

[62]  S. Azuma,et al.  Studies on the OA-6129 group of antibiotics, new carbapenem compounds. I. Taxonomy, isolation and physical properties. , 1982, The Journal of antibiotics.

[63]  J. S. Wells,et al.  SQ 27,860, a simple carbapenem produced by species of Serratia and Erwinia. , 1982, The Journal of antibiotics.

[64]  K. Koga,et al.  SYNTHETIC STUDIES ON OPTICALLY ACTIVE β-LACTAMS. STEREOCONTROLLED SYNTHESIS OF CHIRAL THIENAMYCIN INTERMEDIATE FROM D-GLUCOSE , 1982 .

[65]  D. Floyd,et al.  Monobactams. Stereospecific synthesis of (S)-3-amino-2-oxoazetidine-1-sulfonic acids , 1982 .

[66]  M. Young,et al.  Monobactams. The conversion of 6-APA to (S)-3-amino-2-oxoazetidine-1-sulfonic acid and its 3 (RS)-methoxy derivative , 1982 .

[67]  T. Kato,et al.  Asparenomycins A, B and C, new carbapenem antibiotics. III. Structures. , 1982, The Journal of antibiotics.

[68]  R. Reamer,et al.  Stereospecific conversion of penicillin to thienamycin , 1981 .

[69]  R. Woodward,et al.  Structure, reactivity, and biological activity of strained bicyclic .beta.-lactams , 1981 .

[70]  T. Kawasaki,et al.  Structures and absolute configurations of carpetimycins A and B. , 1981, The Journal of antibiotics.

[71]  J. S. Wells,et al.  Monocyclic β-lactam antibiotics produced by bacteria , 1981, Nature.

[72]  P. G. Mattingly,et al.  Synthesis of 2-azetidinones from serinehydroxamates: approaches to the synthesis of 3-aminonocardicinic acid , 1981 .

[73]  M. Muroi,et al.  Sulfazecin and isosulfazecin, novel β-lactam antibiotics of bacterial origin , 1981, Nature.

[74]  R. Southgate,et al.  Olivanic acid analogues. Part 1. Total synthesis of the 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate system and some related β-lactams , 1981 .

[75]  B. Christensen,et al.  A stereocontrolled synthesis of (+)-thienamycin , 1980 .

[76]  P. G. Mattingly,et al.  Synthesis of .beta.-lactams from substituted hydroxamic acids , 1980 .

[77]  T. Ishikura,et al.  Structure and stereochemistry of antibiotic PS-5. , 1980, The Journal of antibiotics.

[78]  K. Coleman,et al.  In vitro synergistic properties of clavulanic acid, with ampicillin, amoxycillin and ticarcillin. , 1980, The Journal of antimicrobial chemotherapy.

[79]  D. Johnston,et al.  Thienamycin total synthesis. 3. Total synthesis of (.+-.)-thienamycin and (.+-.)-8-epithienamycin , 1980 .

[80]  E. Gordon,et al.  Sulfenyl transfer rearrangement of sulfenimines (thiooximes). A novel synthesis of 7.alpha.-methoxycephalosporins and 6.alpha.-methoxypenicillins , 1980 .

[81]  P. G. Mattingly,et al.  Titanium trichloride reduction of substituted N-hydroxy-2-azetidinones and other hydroxamic acids , 1980 .

[82]  R. Southgate,et al.  Total synthesis of olivanic acids and related compounds: preparation of (±)-MM 22383 and (±)-N-acetyldehydrothienamycin , 1980 .

[83]  R. Southgate,et al.  Olivanic acids and related compounds: total synthesis of (±)-PS-5 and (±)-6-epi PS-5 , 1980 .

[84]  D. Melillo,et al.  A practical synthesis of (±)-thienamycin , 1980 .

[85]  A. Brown,et al.  Structures of olivanic acid derivatives MM 22380, MM 22381, MM 22382 and MM 22383; four new antibiotics isolated from Streptomyces olivaceus. , 1979, The Journal of antibiotics.

[86]  M. Young,et al.  Synthesis of 2-, 4-, and 7-methylthio-substituted cephalosporins , 1979 .

[87]  K. H. Dickinson,et al.  Synthesis of 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylates: the olivanic acid ring system , 1979 .

[88]  M. Hashimoto,et al.  Total synthesis of monocyclic β-lactam antibiotics, nocardicin A and D , 1979 .

[89]  M. Gilpin,et al.  A new total synthesis of (±)-clavulanic acid , 1979 .

[90]  P. Lombardi,et al.  From the penicillin to the nocardicin skeleton: an alternative route , 1979 .

[91]  L. Cama.  Total synthesis of thienamycin analogues. I. Synthesis of the thienamycin nucleus and dl-descysteaminylthienamycin. , 1978 .

[92]  O. Hensens,et al.  Structure and absolute configuration of thienamycin , 1978 .

[93]  G. Koppel,et al.  Total synthesis of nocardicin A. Synthesis of 3-ANA and nocardicin A , 1978 .

[94]  D. Johnston,et al.  Total synthesis of (.+-.)-thienamycin , 1978 .

[95]  M. Gilpin,et al.  Total synthesis of (±)-clavulanic acid , 1977 .

[96]  A. J. Eglington,et al.  Structures of olivanic acid derivatives MM 4550 and MM 13902; two new, fused β-lactams isolated from Streptomyces olivaceus , 1977 .

[97]  M. Hashimoto,et al.  Nocardicin A, a new monocyclic beta-lactam antibiotic II. Structure determination of nocardicins A and B. , 1976, The Journal of antibiotics.

[98]  A. Brown,et al.  Naturally-occurring beta-lactamase inhibitors with antibacterial activity. , 1976, The Journal of antibiotics.

[99]  S. Haber,et al.  Letter: Stereospecific synthesis of penicillins. Conversion from a peptide precursor. , 1976, Journal of the American Chemical Society.

[100]  H. Imanaka,et al.  NOCARDICIN A, A NEW MONOCYCLIC β-LACTAM ANTIBIOTIC , 1976 .

[101]  S. Nakatsuka,et al.  BIOGENETIC-TYPE SYNTHESIS OF PENICILLIN-CEPHALOSPORIN ANTIBIOTICS PART 1, A STEREOCONTROLLED SYNTHESIS OF THE PENAM- AND CEPHEM-RING SYSTEMS FROM AN ACYCLIC TRIPEPTIDE EQUIVALENT , 1975 .

[102]  M. Fukushima,et al.  A novel general method for synthesizing 7α-methoxycephalosporins , 1975 .

[103]  P. Beeby,et al.  A NEW TOTAL SYNTHESIS OF (+-)-DESACETYLCEPHALOTHIN LACTONE, A SYNTHESIS OF NOVEL FURO(3,4-C)CEPHAMS , 1974 .

[104]  J. E. Dolfini,et al.  Synthesis of 7.alpha.-methoxycephalosporins , 1974 .

[105]  R. Firestone,et al.  Total synthesis of beta-lactam antibiotics. IV. Epimerization of 6(7)-aminopenicillins and -cephalosporins from alpha to beta. , 1974, The Journal of organic chemistry.

[106]  J. R. Hoover,et al.  Stereospecific synthesis of C-6(7) methoxypenicillin and cephalosporin derivatives , 1973 .

[107]  Koppel Ga,et al.  Functionalization of C 6(7) of penicillins and cephalosporins. A one-step stereoselective synthesis of 7- -methoxycephalosporin C. , 1973 .

[108]  M. Young,et al.  Synthesis of 6-methylthiopenicillins and 7-heteroatom-substituted cephalosporins. , 1973, The Journal of organic chemistry.

[109]  B. Christensen,et al.  Total synthesis of β-lactam antibiotics II. (±)-cephalothin , 1973 .

[110]  T. Beattie,et al.  Substituted penicillin and cephalosporin derivatives. I. Stereospecific introduction of the C-6(7) methoxy group. , 1972, Journal of the American Chemical Society.

[111]  R. Cooper.  Structural studies on penicillin derivatives. 8. A possible model biosynthetic route to penams and cephems. , 1972, Journal of the American Chemical Society.

[112]  H. Bickel,et al.  Neue β‐Lactam‐Antibiotika. Über die Darstellung der «7‐Aminocephalocillansäure». Modifikationen von Antibiotika, 4. Mitteilung [1] , 1972 .

[113]  Ramanathan Nagarajan,et al.  Beta-lactam antibiotics from Streptomyces. , 1971, Journal of the American Chemical Society.

[114]  R. Woodward.  Recent advances in the chemistry of natural products. , 1966, Pure and applied chemistry. Chimie pure et appliquee.

[115]  S. Pan,et al.  Chemical conversion of desacetylcephalothin lactone into desacetylcephalothin. The final link in a total synthesis of cephalosporanic acid derivatives. , 1970, Journal of medicinal chemistry.

[116]  J. E. Dolfini,et al.  Synthesis of dehydrothiazines related to deacetylcephalosporin lactones. An alternate total synthesis of deacetylcephalosporin lactones. , 1969, The Journal of organic chemistry.

[117]  A. Bose,et al.  Studies on lactams. X. Total synthesis of 5,6-trans-penicillin V methyl ester. , 1968, Journal of the American Chemical Society.

[118]  R. Woodward,et al.  The Total Synthesis of Cephalosporin C1 , 1966 .

[119]  J. C. Sheehan,et al.  The Total and Partial General Syntheses of the Penicillins , 1962 .

[120]  M. Hawthorne.  TRIALKYLAMINE ALKYLBORANES AND A NEW SYNTHESIS OF BORAZOLES , 1959 .

[121]  J. C. Sheehan,et al.  THE TOTAL SYNTHESIS OF PENICILLIN V , 1957 .